3-(3,4-dihydro-2H-benzo [1,4]oxazin-6-yl)-1H-pyrimidin-2,4-dione compounds as herbicides

ABSTRACT

The present invention relates to uracils of formula I 
                         
wherein the variables are defined according to the description, processes and intermediates for preparing the uracils of the formula I, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one uracil of the formula I to act on plants, their seed and/or their habitat.

The present invention relates to uracils of the general formula Idefined below and to their use as herbicides. Moreover, the inventionrelates to compositions for crop protection and to a method forcontrolling unwanted vegetation.

WO 90/15057 for example describes inter alia structurally similarcompounds for which herbicidal action is stated, which differ from theuracils I according to the present invention in that thebenzo[1,4]oxazine ring is preferably unsubstituted in the 2-position orcarries an alkyl group, whereas the uracils of formula I according tothe present invention are substituted in said position by at least onehalogen atom.

However, the herbicidal properties of these known compounds with regardto the harmful plants are not always entirely satisfactory.

It is therefore an object of the present invention to provide uracilshaving improved herbicidal action. To be provided are in particularuracils which have high herbicidal activity, in particular even at lowapplication rates, and which are sufficiently compatible with cropplants for commercial utilization.

These and further objects are achieved by the uracils of the formula I,defined below, and by their agriculturally suitable salts.

Accordingly, the present invention provides uracils of formula I

-   -   wherein    -   R¹ is hydrogen or halogen;    -   R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,        C₃-C₆-haloalkynyl, C₁-C₆-alkoxy or C₃-C₆-cycloalkyl-C₁-C₆-alkyl;    -   R³ is hydrogen or halogen;    -   R⁴ is halogen;    -   R⁵ is hydrogen, NH₂, C₁-C₆-alkyl or C₃-C₆-alkynyl;    -   R⁶ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   R⁷ is hydrogen or C₁-C₆-alkyl;    -   X is O or S; and    -   Y is O or S;    -   including their agriculturally acceptable salts.

The present invention also provides herbicidally active compositionscomprising at least one uracil of formula I and at least one furthercompound selected from herbicidal active compounds B and safeners C.

-   -   The present invention also provides the use of uracils of the        general formula I as herbicides, i.e. for controlling harmful        plants.    -   The present invention also provides mixtures comprising at least        one uracil of the formula I and auxiliaries customary for        formulating crop protection agents.    -   The present invention furthermore provides a method for        controlling unwanted vegetation where a herbicidal effective        amount of at least one uracil of the formula I is allowed to act        on plants, their seeds and/or their habitat. Application can be        done before, during and/or after the emergence of the        undesirable plants.    -   Moreover, the invention relates to processes and intermediates        for preparing uracils of the formula I.

Further embodiments of the present invention are evident from theclaims, the description and the examples. It is to be understood thatthe features mentioned above and still to be illustrated below of thesubject matter of the invention can be applied not only in thecombination given in each particular case but also in othercombinations, without leaving the scope of the invention.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation” and “harmful plants”are synonyms.

If the uracils of formula I as described herein are capable of forminggeometrical isomers, for example E/Z isomers, it is possible to useboth, the pure isomers and mixtures thereof, in the compositionsaccording to the invention.

If the uracils of formula I as described herein have one or more centersof chirality and, as a consequence, are present as enantiomers ordiastereomers, it is possible to use both the pure enantiomers anddiastereomers and their mixtures in the compositions according to theinvention.

If the uracils of formula I as described herein have functional groups,which can be ionized, they can also be used in the form of theiragriculturally acceptable salts or mixtures thereof.

In general, the salts of those cations are suitable whose cations haveno adverse effect on the action of the active compounds (“agriculturalacceptable”). Preferred cations are the ions of the alkali metals,preferably of lithium, sodium and potassium, of the alkaline earthmetals, preferably of calcium and magnesium, and of the transitionmetals, preferably of manganese, copper, zinc and iron, furthermoreammonium and substituted ammonium (hereinafter also termed asorganoammonium) in which one to four hydrogen atoms are replaced byC₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,methylammonium, isopropylammonium, dimethylammonium,diisopropylammonium, trimethylammonium, tetramethylammonium,tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium,benzyltrimethylammonium, benzyltriethylammonium, furthermore phosphoniumions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium such astrimethyl-sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogenphosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate.

The organic moieties mentioned in the definition of the variablesmentioned herein, especially with regard to R¹ to R⁷, are—like the termhalogen—collective terms for individual enumerations of the individualgroup members. The term halogen denotes in each case fluorine, chlorine,bromine or iodine. All hydrocarbon chains, i.e. all alkyl, can bestraight-chain or branched, the prefix C_(n)-C_(m) denoting in each casethe possible number of carbon atoms in the group.

Examples of such meanings are:

-   -   C₁-C₄-alkyl and also the C₁-C₄-alkyl moieties of        C₃-C₈-cycloalkyl-C₁-C₄-alkyl: for example CH₃, C₂H₅, n-propyl,        and CH(CH₃)₂ n-butyl, CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ and C(CH₃)₃;    -   C₁-C₆-alkyl and also the C₁-C₆-alkyl moieties of        C₁-C₆-alkyoxy-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and        also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,        3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,        1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,        2-methylpentyl, 3-methylpentyl, 4-methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or        1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl,        1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;    -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which        is partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl,        1,1,2,2,-tetrafluoroethyl and        1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;    -   C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also,        for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,        5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl,        6-bromohexyl, 6-iodohexyl and trisdecafluorohexyl;    -   C₃-C₆-cycloalkyl and also the cycloalkyl moieties of        C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-cycloalkyxy: monocyclic        saturated hydrocarbons having 3 to 6 ring members, such as        cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;    -   C₃-C₆-alkenyl: for example 1-propenyl, 2-propenyl,        1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,        1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,        2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,        4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,        3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,        3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,        3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,        1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   C₂-C₆-alkenyl and the alkenyl moieties of C₂-C₆-alkenyloxy,        C₂-C₆-haloalkenyloxy: C₃-C₆-alkenyl as mentioned above, and also        ethenyl;

C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, for example 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl,2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl,2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl,2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl,3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or2,3-dibromobut-2-en-1-yl;

-   -   C₃-C₆-alkynyl and also the C₃-C₆-alkynyl moieties of        C₃-C₆-alkynyloxy: for example 1-propynyl, 2-propynyl, 1-butynyl,        2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl,        2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,        1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl,        1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl,        2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,        1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,        2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl,        4-methyl-1-pentynyl, 4-methyl-2-pentynyl,        1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,        1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,        3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,        2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;    -   C₃-C₆-haloalkynyl and also the C₃-C₆-haloalkynyl moieties of        C₃-C₆-haloalkynyloxy: a C₃-C₆-alkynyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,        3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl,        3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,        4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,        4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,        5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or        6-iodohex-5-yn-1-yl;    -   C₁-C₄-alkoxy and also the C₁-C₄-alkoxy moieties of        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-alkylthio-C₂-C₄-alkoxy: for        example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy,        1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;    -   C₁-C₆-alkoxy and also the C₁-C₆-alkoxy moieties of        C₁-C₆-haloalkoxy, C₁-C₆-cyanoalkoxy: C₁-C₄-alkoxy as mentioned        above, and also, for example, pentoxy, 1-methylbutoxy,        2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy,        1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy,        hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,        4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,        1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,        3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,        1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,        1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;    -   C₁-C₄-alkylthio and also the C₁-C₄-alkylithio moieties of        C₁-C₄-alkylthio-C₂-C₄-alkoxy: for example methylthio, ethylthio,        propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,        2-methylpropylthio and 1,1-dimethylethylthio;    -   C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and also,        for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,        3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,        hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,        1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,        4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutylthio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;    -   aryl and also the aryl moiety of aryloxy: a mono- to trinulear        aromatic carbocycle having 6 to 14 ring members, such as for        example, phenyl, maphthyl, anthrav'cenyl and phenanthrenyl.

The preferred embodiments of the invention mentioned herein below haveto be understood as being preferred either independently from each otheror in combination with one another.

According to a preferred embodiment of the invention preference is alsogiven to those uracils of formula I, wherein the variables, eitherindependently of one another or in combination with one another, havethe following meanings:

R¹ is hydrogen;

-   -   is also preferably halogen,    -   particularly preferred F or Cl,    -   especially preferred F;        R² is C₃-C₆-alkynyl or C₃-C₆-haloalkynyl,    -   preferably C₃-alkynyl or C₃-haloalkynyl,    -   particularly preferred CH₂C≡CH, CH₂C≡CCl or CH₂C≡CBr;    -   is also preferably C₃-C₆-alkynyl or        C₃-C₆-cycloalkyl-C₁-C₆-alkyl,    -   particularly preferred propargyl or cyclopropylmethyl;    -   is also preferably C₃-C₆-alkynyl, preferably C₃-alkynyl;        particularly preferred CH₂C≡CH;    -   is also preferably C₃-C₆-haloalkynyl, preferably C₃-haloalkynyl,    -   particularly preferred CH₂C≡CCl or CH₂C≡CBr;        R³ is hydrogen;    -   is also preferably halogen, particularly preferred F;    -   is also preferably hydrogen or F;        R⁴ is F;        R⁵ is hydrogen, NH₂ or C₁-C₆-alkyl,    -   preferably NH₂ or C₁-C₄-alkyl,    -   particularly preferred NH₂ or CH₃;    -   is also preferably C₁-C₆-alkyl,    -   preferably C₁-C₄-alkyl,    -   particularly preferred CH₃;        R⁶ is C₁-C₆-alkyl or C₁-C₆-haloalkyl,    -   preferably C₁-C₄-alkyl or C₁-C₄-haloalkyl,    -   more preferred C₁-C₄-haloalkyl;    -   particularly preferred C₁-C₂-haloalkyl;    -   especially preferred CF₃        R⁷ is hydrogen;    -   is also preferably C₁-C₆-alkyl,    -   preferably C₁-C₄-alkyl,    -   particularly preferred CH₃;        X is O,    -   is also preferably S;        Y is O,    -   is also preferably S.

Particular preference is given to uracils of formula I, wherein R⁴ is F,R⁵ is CH₃, R⁶ is CF₃, R⁷ is hydrogen, X is O and Y is O, and whichherein below are also referred to as uracils of formula Ia:

-   -   wherein the variables R¹, R² and R³ have the meanings, in        particular the preferred meanings, as defined above.

Special preference is given to uracils of the formulae Ia1 to Ia60 oftable A, where the definitions of the variables R¹, R² and R³ are ofparticular importance for the compounds according to the invention notonly in combination with one another but in each case also on their own:

TABLE A no. R¹ R² R³ Ia1 H H H Ia2 H CH₃ H Ia3 H C₂H₅ H Ia4 H CH₂—C₂H₅ HIa5 H CH(CH₃)₂ H Ia6 H CH₂—CH₂—(CH₃)₂ H Ia7 H CH₂—CH═CH₂ H Ia8 H CH₂C≡CHH Ia9 H CH₂C≡C—Cl H Ia10 H CH₂C≡C—Br H Ia11 F H H Ia12 F CH₃ H Ia13 FC₂H₅ H Ia14 F CH₂—C₂H₅ H Ia15 F CH(CH₃)₂ H Ia16 F CH₂—CH₂—(CH₃)₂ H Ia17F CH₂—CH═CH₂ H Ia18 F CH₂C≡CH H Ia19 F CH₂C≡C—Cl H Ia20 F CH₂C≡C—Br HIa21 Cl H H Ia22 Cl CH₃ H Ia23 Cl C₂H₅ H Ia24 Cl CH₂—C₂H₅ H Ia25 ClCH(CH₃)₂ H Ia26 Cl CH₂—CH₂—(CH₃)₂ H Ia27 Cl CH₂—CH═CH₂ H Ia28 Cl CH₂C≡CHH Ia29 Cl CH₂C≡C—Cl H Ia30 Cl CH₂C≡C—Br H Ia31 H H F Ia32 H CH₃ F Ia33 HC₂H₅ F Ia34 H CH₂—C₂H₅ F Ia35 H CH(CH₃)₂ F Ia36 H CH₂—CH₂—(CH₃)₂ F Ia37H CH₂—CH═CH₂ F Ia38 H CH₂C≡CH F Ia39 H CH₂C≡C—Cl F Ia40 H CH₂C≡C—Br FIa41 F H F Ia42 F CH₃ F Ia43 F C₂H₅ F Ia44 F CH₂—C₂H₅ F Ia45 F CH(CH₃)₂F Ia46 F CH₂—CH₂—(CH₃)₂ F Ia47 F CH₂—CH═CH₂ F Ia48 F CH₂C≡CH F Ia49 FCH₂C≡C—Cl F Ia50 F CH₂C≡C—Br F Ia51 Cl H F Ia52 Cl CH₃ F Ia53 Cl C₂H₅ FIa54 Cl CH₂—C₂H₅ F Ia55 Cl CH(CH₃)₂ F Ia56 Cl CH₂—CH₂—(CH₃)₂ F Ia57 ClCH₂—CH═CH₂ F Ia58 Cl CH₂C≡CH F Ia59 Cl CH₂C≡C—Cl F Ia60 Cl CH₂C≡C—Br F

Also preferred are the uracils of formula Ib, particularly preferred theuracils of formulae Ib1 to Ib60, which differ from the correspondinguracils of formulae Ia1 to Ia60 only in that R⁵ is NH₂:

Also preferred are the uracils of formula Ic, particularly preferred theuracils of formulae Ic1 to Ic60, which differ from the correspondinguracils of formulae Ia1 to Ia60 only in that R⁵ is hydrogen:

The uracils of formula I according to the invention can be prepared bystandard processes of organic chemistry, for example by reaction of aniso(thio)cyanate of the formula II with an enamine of the formula III:

The variables R¹ to R⁷, X and Y are each as defined above, preferably asdefined with preference.

In a preferred embodiment of this reaction of an isocyanate of theformula II with an enamine of the formula III, R⁵ is preferablyhydrogen, C₁-C₆-alkyl or C₃-C₆-alkynyl; more preferably hydrogen orC₁-C₆-alkyl, most preferably hydrogen.

L¹ is a nucleophilically displaceable leaving group;

-   -   preferably C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-alkylthio-C₂C₄-alkoxy,        C₂-C₆-alkenyloxy, C₂-C₆-haloalkenyloxy, C₃-C₆-alkynyloxy,        C₃-C₆-haloalkynyloxy, C₃-C₆-cycloalkyloxy, C₁-C₆-cyanoalkoxy or        benzyloxy,        -   which may itself be partly or fully halogenated on the            phenyl ring and/or may be substituted by from one to three            radicals from the group of cyano, nitro, C₁-C₄-alkyl,            C₁-C₄-alkoxy and C₁-C₄-alkylthio;    -   more preferably C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₂-C₆-alkenyloxy,        C₂-C₆-haloalkenyloxy, C₃-C₆-alkynyloxy or C₃-C₆-haloalkynyloxy;    -   very preferably C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy,        C₂-C₆-alkenyloxy or C₃-C₆-alkynyloxy;    -   particularly preferably C₁-C₆-alkoxy.

This reaction of the iso(thio)cyanates of the formula II with enaminesof the formula III are usually carried out for example from −20° C. to80° C. in an inert organic solvent in the presence of a base (e.g. WO05/054208).

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, diethylene glycoldimethyl ether, anisole and tetrahydrofuran, nitriles such asacetonitrile and propionitrile, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, carboxylic esterssuch as butyl acetate, and also dimethyl sulfoxide, dimethylformamide,dimethylacetamide and N-methylpyrrolidone; more preferablydimethylformamide, dimethylacetamide and N-methylpyrrolidone.

It is also possible to use mixtures of the solvents mentioned.

Useful bases are generally inorganic compounds such as alkali metal andalkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as lithium carbonate, sodium carbonate, potassium carbonate,calcium carbonate and cesium carbonate, and also alkali metalhydrogencarbonates such as sodium hydrogencarbonate, organometalliccompounds, especially alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkali metal and alkaline earth metalalkoxides such as lithium methoxide, sodium methoxide, sodium ethoxide,potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxideand dimethoxymagnesium, and also organic bases, for example tertiaryamines such as trimethylamine, triethylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine and 4-dimethylaminopyridine, and also bicyclic amines.Particular preference is given to alkali metal and alkaline earth metalhydroxides, alkali metal and alkaline earth metal carbonates and alsoalkali metal and alkaline earth metal alkoxides.

The bases are generally used in excess, based on the isocyanate of theformula II, and they may also be used as the solvent. It may beadvantageous to add the base offset over a period of time.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if appropriate,chromatographic purification of the crude product. Some of theintermediates and end products are obtained in the form of viscous oils,which can be purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediatesand the end products are obtained as solid, purification can also becarried out by recrystallisation or digestion.

The iso(thio)cyanates of formula II in turn can be obtained from thecorresponding amine compounds IV:

Suitable (thio)phosgenating agents are phosgene, diphosgene ortriphposgene and each of the respective thio derivatives, diphosgenebeing preferred.

The reaction of the amine IV is usually carried out at from −20° C. tothe boiling point of the reaction mixture, preferably at from 10° C. to200° C., particularly preferably at from 20° C. to 150° C., in an inertorganic solvent and, if appropriate, in the presence of a base (e.g. WO04/39768).

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such asdichloromethane, 1,2-dichloroethane, chloroform and chlorobenzene,ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether, dioxane, anisole and tetrahydrofuran, glycol ethers such asdimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethylether, esters such as ethyl acetate, propyl acetate, methyl isobutyrate,isobutyl acetate, carboxamides such as N,N-dimethylformamide,N-methylpyrrolidone, N,N-dimethylacetamide, nitriles such asacetonitrile and propionitrile, ketones such as acetone, methyl ethylketone, diethyl ketone and tert-butyl methyl ketone, as well asdimethylsulfoxide. Particular preference is given to aromatichydrocarbons such as toluene, o-, m- and p-xylene.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general inorganic compounds such as alkali metaland alkaline earth metal carbonates such as lithium carbonate, potassiumcarbonate and calcium carbonate, as well as alkali metal bicarbonatessuch as sodium bicarbonate, and furthermore organic bases, such astertiary amines such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine, N-methylmorpholine and4-dimethylaminopyridine and also bicyclic amines. Particular preferenceis given to tertiary amines such as triethylamine.

The bases are generally employed in catalytic amounts, however they canalso be employed in equimolar amounts, in excess or, if appropriate, beused as solvent.

Work up can be carried out in a known manner.

The enamines of the formula III also required for the preparation of theuracils of formula I are disclosed in the literature (for example A.Lutz, A. and S. Trotto, J. of Heterocyclic Chem. 1972, 9, 3, 513-522)and can be prepared in accordance.

The uracils of formula I according to the invention can also be preparedby reacting a (thio)carbamate of the formula V with an enamine of theformula III:

The variables R¹ to R⁷, X, Y and L¹ are each as defined above,preferably as defined with preference.

L² is a nucleophilically displaceable leaving group,

-   -   preferably C₁-C₆-alkoxy, C₁-C₆-alkylthio or aryloxy, wherein the        aryl moiety may itself be partly or fully halogenated and/or may        be substituted by from one to three radicals from the group of        cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkylthio;    -   particularly preferably C₁-C₆-alkoxy, C₁-C₆-alkylthio or        phenyloxy, wherein the phenyl moiety may itself be partly or        fully halogenated and/or may be substituted by from one to three        radicals from the group of cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy and C₁-C₄-alkylthio;    -   more preferably C₁-C₆-alkoxy, C₁-C₆-alkylthio or phenyloxy;    -   most preferably C₁-C₆-alkoxy.

This reaction of the (thio)carbamates of the formula V with enamines ofthe formula III is effected typically at temperatures above roomtemperature, for example from 25° C. to 200° C., preferably from 90° C.to 190° C., more preferably from 100° C. to 140° C. in an inert organicsolvent in the presence of a base (e.g. WO 99/31091).

Suitable solvents and bases are those mentioned above with regard to thereaction of the isocyanate of the formula II with an enamine of theformula III.

The (thio)carbamates of the formula V required for the preparation ofthe uracils of formula I may be prepared in analogy to known processes(for example Houben-Weyl, Methoden der organischen Chemie [Methods oforganic chemistry], E5, 1985, p. 972-980, and also VIII, p. 655 and XIpart 2, p. 10) by reacting an amine of the formula IV with a compound ofthe formula X

-   -   wherein R¹ to R⁴, X, Y and L² are each as defined above and L³        is a nucleophilically displaceable leaving group.

The (thio)carbamates of the formula V are novel compounds and, as shownabove, suitable intermediates for the preparation of the uracils offormula I according to the present invention.

Therefore the present invention also relates to (thio)carbamates of theformula V

-   -   wherein    -   R¹ is hydrogen or halogen;    -   R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl,        C₃-C₆-haloalkynyl, C₁-C₆-alkoxy or C₃-C₆-cycloalkyl-C₁-C₆-alkyl;    -   R³ is hydrogen or halogen;    -   R⁴ is halogen;    -   X is O or S;    -   Y is O or S; and    -   L² is a nucleophilically displaceable leaving group,        -   preferably C₁-C₆-alkoxy or C₁-C₆-alkylthio,        -   more preferably C₁-C₆-alkoxy.

With respect to the variables, the particularly preferred embodiments ofthe intermediate (thio)carbamates of the formula V correspond, eitherindependently of one another or in combination with one another, tothose of the variables of R¹, R², R³, R⁴, X and Y of the uracils offormula I.

The compounds of the formula X required for the preparation of the(thio)carbamates of the formula V are disclosed in the literature (forexample Houben-Weyl, Methoden der organischen Chemie, E4, 1983, p. 6-17)and can be prepared accordingly or purchased commercially.

Those uracils of formula I, wherein R⁵ is NH₂, C₁-C₆-alkyl orC₃-C₆-alkynyl, can also be prepared by amination or alkylation of thoseuracils of formula I, wherein R⁵ is H:

The amination or alkylation can be conducted in analogy to knownprocesses (e.g. WO 05/054208; WO06/125746).

The amino compounds IV required for the preparation of the(thio)carbamates of the formula II can be obtained from thecorresponding nitro compounds VI:

Preferred is the amino compound IVa (=amino compound IV wherein R⁴ isfluorine and X is O):

The reduction of the nitro compounds VI is usually carried out at from20° C. to the boiling point of the reaction mixture, preferably at from20° C. to 200° C., particularly preferably at from 20° C. to 100° C., inan inert organic solvent [Organikum, Heidelberg, 1993, pages 320-323].

Suitable reducing agents are nascent H₂; hydrogen in the presence ofcatalytic amounts of transition metals or transition metal compounds, inparticular those of the 8th transition group, preferably Ni, Pd, Pt, Ruor Rh, either as such, in supported form e.g. supported via activatedcarbon, Al, ZrO₂, TiO₂, SiO₂, carbonates and the like, or in compoundssuch as palladium oxide or platinum oxide; or metal hydrides, semimetalhydrides such as aluminium hydride and hydrides derived therefrom suchas lithium aluminium hydride, diisobutylaluminiumhydride, borohydridessuch as diborane or boranates derived therefrom such as sodiumborohydride or lithium borohydride.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, ethers such as diethyl ether, diisopropylether, tert.-butyl methyl ether, dioxane, anisole and tetrahydrofuran,glycol ethers such as dimethyl glycol ether, diethyl glycol ether,diethylene glycol dimethyl ether, esters such as ethyl acetate, propylacetate, methyl isobutyrate, isobutyl acetate, carboxamides such asN,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide,nitriles such as acetonitrile and propionitrile, alcohols such asmethanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol,Particular preference is given to toluene and methanol.

It is also possible to use mixtures of the solvents mentioned.

Work up can be carried out in a known manner.

The nitro compounds VI in turn can be obtained from the correspondingphenyl compounds VII:

The nitration of the phenyl compound VII is usually carried out at from−20° C. to 100° C., particularly preferably at from 0° C. to 20° C.[Organikum, Heidelberg, 1993, pages 553-557].

Suitable nitrating agents are mixtures of H₂SO_(4 conc) andHNO_(3 conc), preferably in a range of 50:1 to 1:50, more preferably20:1 to 1:20, especially preferred in a range of 10:1 to 1:10.

Work up can be carried out in a known manner.

Those nitro compounds VI, wherein R² is C₃-C₆-alkenyl,C₃-C₆-haloalkenyl, C₃-C₆-alkynyl or C₃-C₆-haloalkynyl, preferablyC₃-C₆-alkynyl, can also be prepared by alkylation of nitro compounds VI,wherein R² is H:

This reaction is usually carried out at from −78° C. to the boilingpoint of the reaction mixture, preferably at from −40° C. to 100° C.,particularly preferably at from −20° C. to 30° C., in an inert organicsolvent in the presence of a base [WO 02/066471].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such asdichloromethane, 1,2-dichloroethane, chloroform and chlorobenzene,ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether, dioxane, anisole and tetrahydrofuran, glycol ethers such asdimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethylether, esters such as ethyl acetate, propyl acetate, methyl isobutyrate,isobutyl acetate, carboxamides such as N,N-dimethylformamide,N-methylpyrrolidone, N,N-dimethylacetamide, nitriles such asacetonitrile and propionitrile, ketones such as acetone, methyl ethylketone, diethyl ketone and tert-butyl methyl ketone, as well asdimethylsulfoxide. Particular preference is given to ethers such asdiethyl ether, diisopropyl ether, tert.-butyl methyl ether, dioxane,anisole and tetrahydrofuran. It is also possible to use mixtures of thesolvents mentioned.

Suitable bases are, in general inorganic compounds such as alkali metaland alkaline earth metal hydrides such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride, alkali metal andalkaline earth metal carbonates such as lithium carbonate, potassiumcarbonate and calcium carbonate, as well as alkali metal bicarbonatessuch as sodium bicarbonate, alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide, potassium tert-pentoxide anddimethoxymagnesium, and furthermore organic bases, such as tertiaryamines such as trimethylamine, triethylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine, N-methylmorpholine and 4-dimethylaminopyridine and alsobicyclic amines. Particular preference is given to tertiary amines suchas trimethylamine, triethylamine, diisopropylethylamine and alkali metaland alkaline earth metal alkoxides such as sodium methoxide, sodiumethoxide, potassium ethoxide,

The bases are generally employed in catalytic amounts; however they canalso be employed in equimolar amounts, in excess or, if appropriate, beused as solvent.

Work up can be carried out in a known manner.

The phenyl compounds VII in turn can be obtained from the correspondingacetamides VIII:

The cyclisation of the acetamide VIII is usually carried out at from 0°C. to the boiling point of the reaction mixture, preferably at from 0°C. to 140° C., particularly preferably at from 20° C. to 120° C., in aninert organic solvent in the presence of a base [WO 02/066471].

L⁴ is halogen selected from Cl, Br, I; preferably Cl or Br; mostpreferably Cl, also most preferably Br.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such asdichloromethane, 1,2-dichloroethane, chloroform and chlorobenzene,ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether, dioxane, anisole and tetrahydrofuran, glycol ethers such asdimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethylether, esters such as ethyl acetate, propyl acetate, methyl isobutyrate,isobutyl acetate, carboxamides such as N,N-dimethylformamide,N-methylpyrrolidone, N,N-dimethylacetamide, nitriles such asacetonitrile and propionitrile, as well as dimethylsulfoxide.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general Inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxide such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal and alkaline earth metal carbonates suchas lithium carbonate, potassium carbonate and calcium carbonate, as wellas alkali metal bicarbonates such as sodium bicarbonate, metal organiccompounds, preferably alkali metal alkyls such as methyl lithium, butyllithium and phenyl lithium, alkyl magnesium halides such as methylmagnesium chloride as well as alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide, potassium tert-pentoxide anddimethoxymagnesium, and furthermore organic bases, such as tertiaryamines such as trimethylamine, triethylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine, N-methylmorpholine and 4-dimethylaminopyridine and alsobicyclic amines. Particular preference is given to1,8-Diazabicyclo[5.4.0]undec-7-en (DBU).

The bases are generally employed in catalytic amounts, however they canalso be employed in equimolar amounts, in excess or, if appropriate, beused as solvent.

Work up can be carried out in a known manner.

The acetamides VIII in turn can be obtained from the correspondingphenol IX:

This reaction is usually carried out at from −78° C. to the boilingpoint of the reaction mixture, preferably at from −40° C. to 100° C.,particularly preferably at from −20° C. to 30° C., in an inert organicsolvent in the presence of a base [WO 02/066471].

L⁴ is halogen selected from Cl, Br, I; preferably Cl or Br; mostpreferably Cl, also most preferably Br.

L⁵ is a known activating group for acylations, e.g. halogen orC₁-C₆-alkoxy, preferably Cl or C₁-C₆-alkoxy, most preferably Cl, OCH₃ orOC₂H₅.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and mixtures of C₃-C₈-alkanes, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such asdichloromethane, 1,2-dichloroethane, chloroform and chlorobenzene,ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether, dioxane, anisole and tetrahydrofuran, glycol ethers such asdimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethylether, esters such as ethyl acetate, propyl acetate, methyl isobutyrate,isobutyl acetate, carboxamides such as N,N-dimethylformamide,N-methylpyrrolidone, N,N-dimethylacetamide, nitriles such asacetonitrile and propionitrile, ketones such as acetone, methyl ethylketone, diethyl ketone and tert-butyl methyl ketone, as well asdimethylsulfoxide.

Particular preference is given to ethers such as diethyl ether,diisopropyl ether, tert.-butyl methyl ether, dioxane, anisole andtetrahydrofuran.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general inorganic compounds such as alkali metaland alkaline earth metal hydrides such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride, alkali metal andalkaline earth metal carbonates such as lithium carbonate, potassiumcarbonate and calcium carbonate, as well as alkali metal bicarbonatessuch as sodium bicarbonate, alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide, potassium tert-pentoxide anddimethoxymagnesium, and furthermore organic bases, such as tertiaryamines such as trimethylamine, triethylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine, N-methylmorpholine and 4-dimethylaminopyridine and alsobicyclic amines. Particular preference is given to tertiary amines suchas trimethylamine, triethylamine, diisopropylethylamine and alkali metaland alkaline earth metal alkoxides such as sodium methoxide, sodiumethoxide, potassium ethoxide,

The bases are generally employed in catalytic amounts, however they canalso be employed in equimolar amounts, in excess or, if appropriate, beused as solvent.

Work up can be carried out in a known manner.

The phenols IX required for the preparation of the acetamides VIII areknown from the literature [WO 02/066471] or they can be prepared inaccordance with the literature cited and/or are commercially available.

The compounds X required for the preparation of the acetamides VIII arecommercially available.

With regard to the educts mentioned for the preparation of the compoundsof formula I, the variables mentioned in connection with the educts havethe same meaning, preferably the preferred meaning as mentioned hereinwith regard to the respective variables in formula I.

The uracils of formula I are suitable as herbicides. They are suitableas such or as an appropriately formulated composition (herbicidalcomposition). As used in this application, the terms “formulatedcomposition” and “herbicidal composition” are synonyms. The herbicidalcompositions comprising the uracils of formula I control vegetation onnon-crop areas very efficiently, especially at high rates ofapplication. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method in question, the uracils of formulaI or compositions comprising them can additionally be employed in afurther number of crop plants for eliminating undesirable plants.Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera and Zea mays.

Preferred crops are the following: Arachis hypogaea, Beta vulgaris spec.altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeumvulgare, Juglans regia, Lens culinaris, Linum usitatissimum,Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis,Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghumbicolor (S. vulgare), Triticale, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera and Zea mays.

The uracils of formula I according to the invention can also be used ingenetically modified plants. The term “genetically modified plants” isto be understood as plants, which genetic material has been modified bythe use of recombinant DNA techniques in a way that under naturalcircumstances it cannot readily be obtained by cross breeding, mutationsor natural recombination. Typically, one or more genes have beenintegrated into the genetic material of a genetically modified plant inorder to improve certain properties of the plant. Such geneticmodifications also include but are not limited to targetedpost-translational modification of protein(s), oligo- or polypeptidese.g. by glycosylation or polymer additions such as prenylated,acetylated or farnesylated moieties or PEG moieties. Plants that havebeen modified by breeding, mutagenesis or genetic engineering, e.g. havebeen rendered tolerant to applications of specific classes ofherbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors;acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g.U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S.Pat. No. 6,222,100, WO 01/82685, WO 00/026390, WO 97/41218, WO98/002526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/014357, WO03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphatesynthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377);glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A242 236, EP-A 242 246) or oxynil herbicides (see e.g. U.S. Pat. No.5,559,024) as a result of conventional methods of breeding or geneticengineering. Several cultivated plants have been rendered tolerant toherbicides by conventional methods of breeding (mutagenesis), e.g.Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant toimidazolinones, e.g. imazamox. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glypho-sate and glufosinate,some of which are commercially available under the trade namesRound-upReady® (glyphosate-tolerant, Monsanto, U.S.A.) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as ä-endotoxins, e.g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e.g.Photo-rhab-dus spp. or Xenorhabdus spp.; toxins produced by animals,such as scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;aggluti-nins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilbene synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e.g. WO 02/015701). Further examples of such toxins or geneticallymodified plants capable of synthesizing such toxins are disclosed, e.g.,in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878,WO 03/18810 and WO 03/52073. The methods for producing such geneticallymodified plants are generally known to the person skilled in the art andare described, e.g. in the publications mentioned above. Theseinsecticidal proteins contained in the genetically modified plantsimpart to the plants producing these proteins tolerance to harmful pestsfrom all taxonomic groups of arthropods, especially to beetles(Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) andto nematodes (Nematoda). Genetically modified plants capable tosynthesize one or more insecticidal proteins are, e.g., described in thepublications mentioned above, and some of which are commerciallyavailable such as YieldGard® (corn cultivars producing the Cry1Abtoxin), YieldGard® Plus (corn cultivars producing Cry1Ab and Cry3Bb1toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex®RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e.g. EP-A 392 225),plant disease resistance genes (e.g. potato culti-vars, which expressresistance genes acting against Phytophthora infestans derived from theMexican wild potato Solanum bulbocastanum) or T4-lyso-zyme (e.g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e.g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e.g. bio mass production, grain yield, starch content,oil content or protein content), tolerance to drought, salinity or othergrowth-limiting environ-mental factors or tolerance to pests and fungal,bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e.g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e.g. potatoes that produce increased amounts of amylopectin(e.g. Amflora® potato, BASF SE, Germany).

The uracils of formula I according to the invention can also be used incrop plants which are resistant to one or more herbicides owing togenetic engineering or breeding, which are resistant to one or morepathogens such as plant pathogenous fungi owing to genetic engineeringor breeding, or which are resistant to attack by insects owing togenetic engineering or breeding.

Suitable are for example crop plants, preferably corn, wheat, sunflower,sugarcane, cotton, rice, canola, oilseed rape or soybeans, which cropsare resistant to herbicidal PPO inhibitors, or crop plants which, owingto introduction of the gene for Bt toxin by genetic modification, areresistant to attack by certain insects.

Furthermore, it has been found that the uracils of the formula I arealso suitable for the defoliation and/or desiccation of plant parts, forwhich crop plants such as cotton, potato, oilseed rape, sunflower,soybean or field beans, in particular cotton, are suitable. In thisregard there have been found compositions for the desiccation and/ordefoliation of plants, processes for preparing these compositions andmethods for desiccating and/or defoliating plants using the uracils ofthe formula I.

As desiccants, the uracils of the formula I are particularly suitablefor desiccating the above-ground parts of crop plants such as potato,oilseed rape, sunflower and soybean, but also cereals. This makespossible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is madepossible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in citrus fruit,olives and other species and varieties of pernicious fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the controlled defoliation of usefulplants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The uracils of formula I, or the herbicidal compositions comprising theuracils of formula I, can be used, for example, in the form ofready-to-spray aqueous solutions, powders, suspensions, also highlyconcentrated aqueous, oily or other suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for broadcasting,or granules, by means of spraying, atomizing, dusting, spreading,watering or treatment of the seed or mixing with the seed. The use formsdepend on the intended purpose; in any case, they should ensure thefinest possible distribution of the active ingredients according to theinvention.

The herbicidal compositions comprise an herbicidal effective amount ofat least one uracils of the formula I and auxiliaries which arecustomary for the formulation of crop protection agents.

-   -   Examples of auxiliaries customary for the formulation of crop        protection agents are inert auxiliaries, solid carriers,        surfactants (such as dispersants, protective colloids,        emulsifiers, wetting agents and tackifiers), organic and        inorganic thickeners, bactericides, antifreeze agents,        antifoams, optionally colorants and, for seed formulations,        adhesives.    -   The person skilled in the art is sufficiently familiar with the        recipes for such formulations.    -   Examples of thickeners (i.e. compounds which impart to the        formulation modified flow properties, i.e. high viscosity in the        state of rest and low viscosity in motion) are polysaccharides,        such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone        Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and        inorganic sheet minerals, such as Attaclay® (from Engelhard).    -   Examples of antifoams are silicone emulsions (such as, for        example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia),        long-chain alcohols, fatty acids, salts of fatty acids,        organofluorine compounds and mixtures thereof. Bactericides can        be added for stabilizing the aqueous herbicidal formulations.

Examples of bactericides are bactericides based on dichlorophen andbenzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from ThorChemie and Kathon® MK from Rohm & Haas), and also isothiazolinonederivates, such as alkylisothiazolinones and benzisothiazolinones(Acticide MBS from Thor Chemie).

-   -   Examples of antifreeze agents are ethylene glycol, propylene        glycol, urea or glycerol.    -   Examples of colorants are both sparingly water-soluble pigments        and water-soluble dyes. Examples which may be mentioned are the        dyes known under the names Rhodamin B, C.I. Pigment Red 112 and        C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue        15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80,        pigment yellow 1, pigment yellow 13, pigment red 112, pigment        red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1,        pigment orange 43, pigment orange 34, pigment orange 5, pigment        green 36, pigment green 7, pigment white 6, pigment brown 25,        basic violet 10, basic violet 49, acid red 51, acid red 52, acid        red 14, acid blue 9, acid yellow 23, basic red 10, basic red        108.    -   Examples of adhesives are polyvinylpyrrolidone, polyvinyl        acetate, polyvinyl alcohol and tylose.    -   Suitable inert auxiliaries are, for example, the following:        mineral oil fractions of medium to high boiling point, such as        kerosene and diesel oil, furthermore coal tar oils and oils of        vegetable or animal origin, aliphatic, cyclic and aromatic        hydrocarbons, for example paraffin, tetrahydronaphthalene,        alkylated naphthalenes and their derivatives, alkylated benzenes        and their derivatives, alcohols such as methanol, ethanol,        propanol, butanol and cyclohexanol, ketones such as        cyclohexanone or strongly polar solvents, for example amines        such as N-methylpyrrolidone, and water.    -   Suitable carriers include liquid and solid carriers. Liquid        carriers include e.g. non-aqueous solvents such as cyclic and        aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene,        alkylated naphthalenes and their derivatives, alkylated benzenes        and their derivatives, alcohols such as methanol, ethanol,        propanol, butanol and cyclohexanol, ketones such as        cyclohexanone, strongly polar solvents, e.g. amines such as        N-methylpyrrolidone, and water as well as mixtures thereof.    -   Solid carriers include e.g. mineral earths such as silicas,        silica gels, silicates, talc, kaolin, limestone, lime, chalk,        bole, loess, clay, dolomite, diatomaceous earth, calcium        sulfate, magnesium sulfate and magnesium oxide, ground synthetic        materials, fertilizers such as ammonium sulfate, ammonium        phosphate, ammonium nitrate and ureas, and products of vegetable        origin, such as cereal meal, tree bark meal, wood meal and        nutshell meal, cellulose powders, or other solid carriers.    -   Suitable surfactants (adjuvants, wetting agents, tackifiers,        dispersants and also emulsifiers) are the alkali metal salts,        alkaline earth metal salts and ammonium salts of aromatic        sulfonic acids, for example lignosulfonic acids (e.g.        Borrespers-types, Borregaard), phenolsulfonic acids,        naphthalenesulfonic acids (Morwet types, Akzo Nobel) and        dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of        fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates,        lauryl ether sulfates and fatty alcohol sulfates, and salts of        sulfated hexa-, hepta- and octadecanols, and also of fatty        alcohol glycol ethers, condensates of sulfonated naphthalene and        its derivatives with formaldehyde, condensates of naphthalene or        of the naphthalenesulfonic acids with phenol and formaldehyde,        polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-        or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether,        alkylaryl polyether alcohols, isotridecyl alcohol, fatty        alcohol/ethylene oxide condensates, ethoxylated castor oil,        polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers,        lauryl alcohol polyglycol ether acetate, sorbitol esters,        lignosulfite waste liquors and proteins, denaturated proteins,        polysaccharides (e.g. methylcellulose), hydrophobically modified        starches, polyvinyl alcohol (Mowiol types Clariant),        polycarboxylates (BASF SE, Sokalan types), polyalkoxylates,        polyvinylamine (BASF SE, Lupamine types), polyethyleneimine        (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers        thereof.    -   Powders, materials for broadcasting and dusts can be prepared by        mixing or concomitant grinding the active ingredients together        with a solid carrier. Granules, for example coated granules,        impregnated granules and homogeneous granules, can be prepared        by binding the active ingredients to solid carriers.    -   Aqueous use forms can be prepared from emulsion concentrates,        suspensions, pastes, wettable powders or water-dispersible        granules by adding water. To prepare emulsions, pastes or oil        dispersions, the uracils of the formula I, either as such or        dissolved in an oil or solvent, can be homogenized in water by        means of a wetting agent, tackifier, dispersant or emulsifier.        Alternatively, it is also possible to prepare concentrates        comprising active compound, wetting agent, tackifier, dispersant        or emulsifier and, if desired, solvent or oil, which are        suitable for dilution with water.    -   The concentrations of the uracils of the formula I in the        ready-to-use preparations (formulations) can be varied within        wide ranges. In general, the formulations comprise approximately        from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of        at least one active ingredient. The active ingredients are        employed in a purity of from 90% to 100%, preferably 95% to 100%        (according to NMR spectrum).

In the formulation of the uracils of formula I according to the presentinvention the active ingredients, e.g. the uracils of formula I, arepresent in suspended, emulsified or dissolved form. The formulationaccording to the invention can be in the form of aqueous solutions,powders, suspensions, also highly-concentrated aqueous, oily or othersuspensions or dispersions, aqueous emulsions, aqueous microemulsions,aqueous suspo-emulsions, oil dispersions, pastes, dusts, materials forspreading or granules.

-   -   The uracils of formula I according to the present invention can,        for example, be formulated as follows:        1. Products for Dilution with Water        A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other adjuvants are added. The active compound dissolves upondilution with water. This gives a formulation with an active compoundcontent of 10% by weight.

B Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). Dilution with water gives an emulsion. Theformulation has an active compound content of 15% by weight.

D Emulsions

25 parts by weight of active compound are dissolved in 35 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). This mixture is introduced into 30 parts by weightof water by means of an emulsifier (Ultraturrax) and made into ahomogeneous emulsion. Dilution with water gives an emulsion. Theformulation has an active compound content of 25% by weight.

E Suspensions

In an agitated ball mill, 20 parts by weight of active compound arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active compound. The active compound content in theformulation is 20% by weight.

F Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator millwith addition of 25 parts by weight of dispersants, wetters and silicagel. Dilution with water gives a stable dispersion or solution of theactive compound. The active compound content of the formulation is 75%by weight.

H Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts byweight of dispersant, 1 part by weight of gelling agent and 70 parts byweight of water or of an organic solvent are mixed to give a finesuspension. Dilution with water gives a stable suspension with activecompound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associatedwith

99.5 parts by weight of carriers. Current methods here are extrusion,spray-drying or the fluidized bed. This gives granules to be appliedundiluted with an active compound content of 0.5% by weight.

K ULV solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productto be applied undiluted with an active compound content of 10% byweight.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water.

The uracils of the formula I or the herbicidal compositions comprisingthem can be applied pre-, post-emergence or pre-plant, or together withthe seed of a crop plant. It is also possible to apply the herbicidalcomposition or active compounds by applying seed, pretreated with theherbicidal compositions or active compounds, of a crop plant. If theactive ingredients are less well tolerated by certain crop plants,application techniques may be used in which the herbicidal compositionsare sprayed, with the aid of the spraying equipment, in such a way thatas far as possible they do not come into contact with the leaves of thesensitive crop plants, while the active ingredients reach the leaves ofundesirable plants growing underneath, or the bare soil surface(post-directed, lay-by).

In a further embodiment, the uracils of the formula I or the herbicidalcompositions can be applied by treating seed. The treatment of seedscomprises essentially all procedures familiar to the person skilled inthe art (seed dressing, seed coating, seed dusting, seed soaking, seedfilm coating, seed multilayer coating, seed encrusting, seed drippingand seed pelleting) based on the uracils of the formula I according tothe invention or the compositions prepared therefrom. Here, theherbicidal compositions can be applied diluted or undiluted.

-   -   The term “seed” comprises seed of all types, such as, for        example, corns, seeds, fruits, tubers, seedlings and similar        forms. Here, preferably, the term seed describes corns and        seeds. The seed used can be seed of the useful plants mentioned        above, but also the seed of transgenic plants or plants obtained        by customary breeding methods.

The rates of application of the active uracils of formula I according tothe present invention (total amount of uracil I) are from 0.1 g/ha to3000 g/ha, preferably 10 g/ha to 1000 g/ha of active substance (a.s.),depending on the control target, the season, the target plants and thegrowth stage.

-   -   In another preferred embodiment of the invention, the        application rates of the uracils of formula I are in the range        from 0.1 g/ha to 5000 g/ha and preferably in the range from 1        g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha of active        substance (a.s.).    -   In another preferred embodiment of the invention, the        application rate of the uracils of formula I is 0.1 to 1000        g/ha, preferably) to 750 g/ha, more preferably 5 to 500 g/ha, of        active substance.    -   To treat the seed, the uracils of formula I are generally        employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

To broaden the spectrum of action and to achieve synergistic effects,the uracils of the formula I may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating activeingredient groups and then applied concomitantly. Suitable componentsfor mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones,2-hetaroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyl-uracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-uracils, oxadiazoles,oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters,phenylacetic acid and its derivatives, 2-phenylpropionic acid and itsderivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylicacid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas,triazines, triazinones, triazolinones, triazolecarboxamides, uracils,phenyl pyrazolines and isoxazolines and derivatives thereof.

It may be beneficial to apply the uracils of the formula I alone or incombination with other herbicides, or else in the form of a mixture withother crop protection agents, for example together with agents forcontrolling pests or phytopathogenic fungi or bacteria. Also of interestis the miscibility with mineral salt solutions, which are employed fortreating nutritional and trace element deficiencies. Other additivessuch as non-phytotoxic oils and oil concentrates may also be added.

The further herbicidal active component B is preferably selected fromthe herbicides of class b1) to b15):

-   b1) lipid biosynthesis inhibitors;-   b2) acetolactate synthase inhibitors (ALS inhibitors);-   b3) photosynthesis inhibitors;-   b4) protoporphyrinogen-IX oxidase inhibitors,-   b5) bleacher herbicides;-   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP    inhibitors);-   b7) glutamine synthetase inhibitors;-   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);-   b9) mitose inhibitors;-   b10) inhibitors of the synthesis of very long chain fatty acids    (VLCFA inhibitors);-   b11) cellulose biosynthesis inhibitors;-   b12) decoupler herbicides;-   b13) auxin herbicides;-   b14) auxin transport inhibitors; and-   b15) other herbicides selected from the group consisting of    bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,    cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate,    dimethipin, DSMA, dymron, endothal and its salts, etobenzanid,    flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl,    flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine,    fosamine-ammonium, indanofan, indaziflam, maleic hydrazide,    mefluidide, metam, methyl azide, methyl bromide, methyl-dymron,    methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid,    pyributicarb, quinoclamine, triaziflam, tridiphane and    6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS    499223-49-3) and its salts and esters;

Preference is given to those compositions according to the presentinvention comprising at least one herbicide B selected from herbicidesof class b2, b3, b4, b5, b6, b9 and b10.

Particular preference is given to those compositions according to thepresent invention which comprise at least one herbicide B selected fromthe herbicides of class b4, b6 and b10.

Examples of herbicides B which can be used in combination with theuracils of the formula I according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim,clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop,cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden,profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, sethoxydim, tepraloxydim and tralkoxydim, and nonACC herbicides such as benfuresate, butylate, cycloate, dalapon,dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate,orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil,triallate and vernolate;b2) from the group of the ALS inhibitors:Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron,bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, mesosulfuron, metazosulfuron, metsulfuron,metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron,pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron,sulfometuron-methyl, sulfosulfuron, thifensulfuron,thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl andtritosulfuron, imidazolinones such as imazamethabenz,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin andimazethapyr, triazolopyrimidine herbicides and sulfonanilides such ascloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam,metosulam, penoxsulam, pyrimisulfan and pyroxsulam,pyrimidinylbenzoates such as bispyribac, bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac,pyrithiobac-sodium,4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid-1-methylethyl ester (CAS 420138-41-6),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid propyl ester (CAS 420138-40-5),N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine(CAS 420138-01-8) and sulfonylaminocarbonyl-triazolinone herbicides suchas flucarbazone, flucarbazone-sodium, propoxycarbazon,propoxycarbazon-sodium, thiencarbazone and thiencarbazone-methyl. Amongthese, a preferred embodiment of the invention relates to thosecompositions comprising at least one imidazolinone herbicide;b3) from the group of the photosynthesis inhibitors:amicarbazone, inhibitors of the photosystem II, e.g. triazineherbicides, including of chlorotriazine, triazinones, triazindiones,methylthiotriazines and pyridazinones such as ametryn, atrazine,chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone,metribuzin, prometon, prometryn, propazin, simazin, simetryn,terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such aschlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron,fluometuron, isoproturon, isouron, linuron, metamitron,methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon,siduron, tebuthiuron and thiadiazuron, phenyl carbamates such asdesmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrileherbicides such as bromofenoxim, bromoxynil and its salts and esters,ioxynil and its salts and esters, uracils such as bromacil, lenacil andterbacil, and bentazon and bentazon-sodium, pyridate, pyridafol,pentanochlor and propanil and inhibitors of the photosystem I such asdiquat, diquat-dibromide, paraquat, paraquat-dichloride andparaquat-dimetilsulfate. Among these, a preferred embodiment of theinvention relates to those compositions comprising at least one arylurea herbicide. Among these, likewise a preferred embodiment of theinvention relates to those compositions comprising at least one triazineherbicide. Among these, likewise a preferred embodiment of the inventionrelates to those compositions comprising at least one nitrile herbicide;b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin,ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6;

-   S-3100),    N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 452098-92-9),    N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 915396-43-9),    N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 452099-05-7),    N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 45100-03-7),    3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,    1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione    and    2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione;    b5) from the group of the bleacher herbicides:    PDS inhibitors: beflubutamid, diflufenican, fluridone,    fluorochloridone, flurtamone, norflurazon, picolinafen, and    4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine    (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap,    isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen,    sulcotrione, tefuryltrione, tembotrione, topramezone and    bicyclopyrone, bleacher, unknown target: aclonifen, amitrole,    clomazone and flumeturon;    b6) from the group of the EPSP synthase inhibitors:    glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium    (sulfosate);    b7) from the group of the glutamine synthase inhibitors:    bilanaphos (bialaphos), bilanaphos-sodium, glufosinate,    glufosinate-P and glufosinate-ammonium;    b8) from the group of the DHP synthase inhibitors:    asulam;    b9) from the group of the mitose inhibitors:    compounds of group K1: dinitroanilines such as benfluralin,    butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin,    pendimethalin, prodiamine and trifluralin, phosphoramidates such as    amiprophos, amiprophos-methyl, and butamiphos, benzoic acid    herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as    dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam;    compounds of group K2: chlorpropham, propham and carbetamide, among    these, compounds of group K1, in particular dinitroanilines are    preferred;    b10) from the group of the VLCFA inhibitors:    chloroacetamides such as acetochlor, alachlor, butachlor,    dimethachlor, dimethenamid, dimethenamid-P, metazachlor,    metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor,    propisochlor and thenylchlor, oxyacetanilides such as flufenacet and    mefenacet, acetanilides such as diphenamid, naproanilide and    napropamide, tetrazolinones such fentrazamide, and other herbicides    such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone,    piperophos, pyroxasulfone and isoxazoline compounds of the formula    II,

-   -   wherein R²¹, R²², R²³, R²⁴, W, Z and n have the following        meanings:    -   R²¹, R²², R²³, R²⁴ independently of one another hydrogen,        halogen or C₁-C₄-alkyl;    -   W phenyl or monocyclic 5-, 6-, 7-, 8-, 9- or 10-membered        heterocyclyl containing, in addition to carbon ring members one,        two or three same or different heteroatoms selected from oxygen,        nitrogen and sulfur as ring members, wherein phenyl and        heterocyclyl are unsubstituted or carry 1, 2 or 3 substituents        R^(yy) selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkyl and C₁-C₄-haloalkoxy;    -   preferably phenyl or 5- or 6-membered aromatic heterocyclyl        (hetaryl) which contains, in addition to carbon ring members,        one, two or three nitrogen atoms as ring members, wherein phenyl        and hetaryl are unsubstituted or carry 1, 2 or 3 substituents        R^(yy);    -   Z oxygen or NH; and    -   n zero or one;    -   among the isoxazoline compounds of the formula II, preference is        given to isoxazoline compounds of the formula II, wherein    -   R²¹, R²², R²³, R²⁴ independently of one another are H, F, Cl or        methyl;    -   Z is oxygen;    -   n is 0 or 1; and    -   W is phenyl, pyrazolyl or 1,2,3-triazolyl, wherein the three        last-mentioned radicals are unsubstituted or carry one, two or        three substituents R^(yy), especially one of the following        radicals

-   -   -   wherein        -   R²² is halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;        -   R²⁶ is C₁-C₄-alkyl;        -   R²⁷ is halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;        -   R²⁸ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or            C₁-C₄-haloalkoxy;        -   m is 0, 1, 2 or 3; and        -   # denotes the point of attachment to the group CR²³R²⁴;

    -   among the isoxazoline compounds of the formula II, particular        preference is given to those isoxazoline compounds of the        formula II, wherein

    -   R²¹ is hydrogen;

    -   R²² is fluorine;

    -   R²³ is hydrogen or fluorine;

    -   R²⁴ is hydrogen or fluorine;

    -   W is one of the radicals of the formulae W¹, W², W³ or W⁴

-   -   -   wherein # denotes the point of attachment to the group            CR¹³R¹⁴;

    -   Z is oxygen;

    -   n is zero or 1, in particular 1; and

    -   among these, especially preferred are the isoxazoline compounds        of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8        and II.9

-   -   the isoxazoline compounds of the formula II are known in the        art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900        and WO 2007/096576;    -   among the VLCFA inhibitors, preference is given to        chloroacetamides and oxyacetamides;        b11) from the group of the cellulose biosynthesis inhibitors:        chlorthiamid, dichlobenil, flupoxam, isoxaben,        1-Cyclohexyl-5-pentafluorphenyloxy-1⁴-[1,2,4,6]thiatriazin-3-ylamine        and piperazine compounds of formula III

-   -   in which    -   A is phenyl or pyridyl where R^(a) is attached in the        ortho-position to the point of attachment of A to a carbon atom;    -   R^(a) is CN, NO₂, C₁-C₄-alkyl, D-C₃-C₆-cycloalkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        O-D-C₃-C₆-cycloalkyl, S(O)_(q)R^(y), C₂-C₆-alkenyl,        D-C₃-C₆-cycloalkenyl, C₃-C₆-alkenyloxy, C₂-C₆-alkynyl,        C₃-C₆-alkynyloxy, NR^(A)R^(B), tri-C₁-C₄-alkylsilyl,        D-C(═O)—R^(a1), D-P(═O)(R^(a1))₂, phenyl, naphthyl, a 3- to        7-membered monocyclic or 9- or 10-membered bicyclic saturated,        unsaturated or aromatic heterocycle which is attached via carbon        or nitrogen, which contains 1, 2, 3 or 4 heteroatoms selected        from the group consisting of O, N and S, and which may be        partially or fully substituted by groups R^(aa) and/or R^(a1),        and, if R^(a) is attached to a carbon atom, additionally        halogen;        -   R^(y) is C₁-C₆-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,            NR^(A)R^(B) or C₁-C₄-haloalkyl and q is 0, 1 or 2;        -   R^(A), R^(B) independently of one another are hydrogen,            C₁-C₆-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl; together with            the nitrogen atom to which they are attached, R^(A), R^(B)            may also form a five- or six-membered saturated, partially            or fully unsaturated ring which, in addition to carbon            atoms, may contain 1, 2 or 3 heteroatoms selected from the            group consisting of O, N and S, which ring may be            substituted by 1 to 3 groups R^(aa);        -   D is a covalent bond, C₁-C₄-alkylene, C₂-C₆-alkenyl or            C₂-C₆-alkynyl;        -   R^(a1) is hydrogen, OH, C₁-C₈-Alkyl, C₁-C₄-haloalkyl,            C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, C₅-C₆-cycloalkenyl,            C₂-C₈-alkynyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy,            C₃-C₈-alkenyloxy, C₃-C₈-alkynyloxy, NR^(A)R^(B),            C₁-C₆-alkoxyamino, C₁-C₆-alkylsulfonylamino,            C₁-C₆-alkylaminosulfonylamino,            [di-(C₁-C₆)alkylamino]sulfonylamino, C₃-C₆-alkenylamino,            C₃-C₆-alkynylamino, N—(C₂-C₆-alkenyl)-N—(C₁-C₆-alkyl)amino,            N—(C₂-C₆-alkynyl)-N—(C₁-C₆-alkyl)amino,            N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)amino,            N—(C₂-C₆-alkenyl)-N—(C₁-C₆-alkoxy)amino,            N—(C₂-C₆-alkynyl)-N—(C₁-C₆-alkoxy)-amino,            C₁-C₆-alkylsulfonyl, tri-C₁-C₄-alkylsilyl, phenyl, phenoxy,            phenylamino or a 5- or 6-membered monocyclic or 9- or            10-membered bicyclic heterocycle which contains 1, 2, 3 or 4            heteroatoms selected from the group consisting of O, N and            S, where the cyclic groups are unsubstituted or substituted            by 1, 2, 3 or 4 groups R^(aa);        -   R^(aa) is halogen, OH, CN, NO₂, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            S(O)_(q)R^(y), D-C(═O)—R^(a1) and tri-C₁-C₄-alkylsilyl;    -   R^(b) independently of one another are hydrogen, CN, NO₂,        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₃-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, benzyl or        S(O)_(q)R^(y),        -   R^(b) together with the group R^(a) or R^(b) attached to the            adjacent ring atom may also form a five- or six-membered            saturated or partially or fully unsaturated ring which, in            addition to carbon atoms, may contain 1, 2 or 3 heteroatoms            selected from the group consisting of O, N and S, which ring            may be partially or fully substituted by R^(aa);    -   p is 0, 1, 2 or 3;    -   R³⁰ is hydrogen, OH, CN, C₁-C₁₂-alkyl, C₃-C₁₂-alkenyl,        C₃-C₁₂-alkynyl, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl,        C₅-C₆-cycloalkenyl, NR^(A)R^(B), S(O)_(n)R^(y),        S(O)_(n)NR^(A)R^(B), C(═O)R⁴⁰, CONR^(A)RB, phenyl or a 5- or        6-membered monocyclic or 9- or 10-membered bicyclic aromatic        heterocycle which contains 1, 2, 3 or 4 heteroatoms selected        from the group consisting of O, N and S, where the cyclic groups        are attached via D¹ and are unsubstituted or substituted by 1,        2, 3 or 4 groups R^(aa), and also the following partially or        fully R^(aa)-substituted groups: C₁-C₄-alkyl, C₃-C₄-alkenyl and        C₃-C₄-alkynyl;        -   R⁴⁰ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy            or C₁-C₄-haloalkoxy;        -   D¹ is carbonyl or a group D;        -   where in groups R¹⁵, R^(a) and their sub-substituents the            carbon chains and/or the cyclic groups may carry 1, 2, 3 or            4 substituents R^(aa) and/or R^(a1);    -   R³¹ is C₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl;    -   R³² is OH, NH₂, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₄-hydroxyalkyl, C₁-C₄-cyanoalkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl or C(═O)R⁴⁰;    -   R³³ is hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl, or R³³        and R³⁴ together are a covalent bond;    -   R³⁴, R³⁵, R³⁶, R³⁷ independently of one another are hydrogen,        halogen, OH, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl and C₃-C₆-cycloalkynyl;    -   R³⁸, R³⁹ independently of one another are hydrogen, halogen, OH,        haloalkyl, NR^(A)R^(B), NR^(A)C(O)R⁴¹, CN, NO₂, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₃-C₆-alkynyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, O—C(O)R⁴¹, phenoxy or benzyloxy, where in        groups R³⁸ and R³⁹ the carbon chains and/or the cyclic groups        may carry 1, 2, 3 or 4 substituents R^(aa);    -   R⁴¹ is C₁-C₄-alkyl or NR^(A)R^(B);    -   among the piperazine compounds of formula III, preference is        given to the piperazine compounds of the formula III, wherein    -   A is phenyl or pyridyl where R^(a) is attached in the        ortho-position to the point of attachment of A to a carbon atom;    -   R^(a) is CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy or D-C(═O)—R^(a1);        -   R^(y) is C₁-C₆-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,            NR^(A)R^(B) or C₁-C₄-haloalkyl and q is 0, 1 or 2;        -   R^(A), R^(B) independently of one another are hydrogen,            C₁-C₆-alkyl, C₃-C₆-alkenyl and C₃-C₆-alkynyl; together with            the nitrogen atom to which they are attached, R^(A), R^(B)            may also form a five- or six-membered saturated, partially            or fully unsaturated ring which, in addition to carbon            atoms, may contain 1, 2 or 3 heteroatoms selected from the            group consisting of O, N and S, which ring may be            substituted by 1 to 3 groups R^(aa);        -   D is a covalent bond or C₁-C₄-alkylene;        -   R^(a1) is hydrogen, OH, C₁-C₈-Alkyl, C₁-C₄-haloalkyl,            C₃-C₆-cycloalkyl;        -   R^(aa) is halogen, OH, CN, NO₂, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            S(O)_(q)R^(y), D-C(═O)—R^(a1) and tri-C₁-C₄-alkylsilyl;    -   R^(b) independently of one another is CN, NO₂, halogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₃-C₆-alkynyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, benzyl or S(O)_(q)R^(y),        -   R^(b) together with the group R^(a) or R^(b) attached to the            adjacent ring atom may also form a five- or six-membered            saturated or partially or fully unsaturated ring which, in            addition to carbon atoms, may contain 1, 2 or 3 heteroatoms            selected from the group consisting of O, N and S, which ring            may be partially or fully substituted by R^(aa);    -   p is 0 or 1;    -   R³⁰ is hydrogen, C₁-C₁₂-alkyl, C₃-C₁₂-alkenyl, C₃-C₁₂-alkynyl,        C₁-C₄-alkoxy or C(═O)R⁴⁰;        -   R⁴⁰ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy            or C₁-C₄-haloalkoxy;        -   where in groups R³⁰, R^(a) and their sub-substituents the            carbon chains and/or the cyclic groups may carry 1, 2, 3 or            4 substituents R^(aa) and/or R^(a1);    -   R³¹ is C₁-C₄-alkyl;    -   R³² is OH, NH₂, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl        or C(═O)R²⁵;    -   R³³ is hydrogen, or R³³ and R³⁴ together are a covalent bond;    -   R³⁴, R³⁵, R³⁶, R³⁷ independently of one another are hydrogen;    -   R³⁸, R³⁹ independently of one another are hydrogen, halogen or        OH;        b12) from the group of the decoupler herbicides:        dinoseb, dinoterb and DNOC and its salts;        b13) from the group of the auxin herbicides:        2,4-D and its salts and esters, 2,4-DB and its salts and esters,        aminopyralid and its salts such as        aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,        benazolin, benazolin-ethyl, chloramben and its salts and esters,        clomeprop, clopyralid and its salts and esters, dicamba and its        salts and esters, dichlorprop and its salts and esters,        dichlorprop-P and its salts and esters, fluoroxypyr,        fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPA and its salts        and esters, MCPA-thioethyl, MCPB and its salts and esters,        mecopropand its salts and esters, mecoprop-P and its salts and        esters, picloram and its salts and esters, quinclorac,        quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and        its salts and esters, and aminocyclopyrachlor and its salts and        esters;        b14) from the group of the auxin transport inhibitors:        diflufenzopyr, diflufenzopyr-sodium, naptalam and        naptalam-sodium;        b15) from the group of the other herbicides: bromobutide,        chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron,        dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate,        dimethipin, DSMA, dymron, endothal and its salts, etobenzanid,        flamprop, flamprop-isopropyl, flamprop-methyl,        flamprop-M-isopropyl, flamprop-M-methyl, flurenol,        flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium,        indanofan, indaziflam, maleic hydrazide, mefluidide, metam,        methyl azide, methyl bromide, methyl-dymron, methyl iodide,        MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb,        quinoclamine, triaziflam, tridiphane and        6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS        499223-49-3) and its salts and esters.

Moreover, it may be useful to apply the uracils of the formula I incombination with safeners. Safeners are chemical compounds which preventor reduce damage on useful plants without having a major impact on theherbicidal action of the uracils of the formula I towards unwantedplants. They can be applied either before sowings (e.g. on seedtreatments, shoots or seedlings) or in the pre-emergence application orpost-emergence application of the useful plant. The safeners and theuracils of the formula I can be applied simultaneously or in succession.

Suitable safeners are e.g. (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids,4,5-dihydro-5,5-diary)-3-isoxazol carboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenonoximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids,phosphorthiolates and N-alkyl-O-phenyl-carbamates and theiragriculturally acceptable salts and their agriculturally acceptablederivatives such amides, esters, and thioesters, provided they have anacid group.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3)and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4).

Especially preferred safeners C are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole,fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride,oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660,CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(R-29148, CAS 52836-31-4).

Particularly preferred safeners C are benoxacor, cloquintocet,cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole,isoxadifen, mefenpyr, naphthalic anhydride,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3)and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are knownherbicides and safeners, see, for example, The Compendium of PesticideCommon Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke,R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart,1995. Further herbicidal active compounds are known from WO 96/26202, WO97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991 andfrom W. Kramer et al. (ed.) “Modern Crop Protection Compounds”, Vol. 1,Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 1-component compositioncomprising an active compound combination comprising at least one uracilof the formula I and at least one further active compound, preferablyselected from the active compounds of groups b1 to b15, and at least onesolid or liquid carrier and/or one or more surfactants and, if desired,one or more further auxiliaries customary for crop protectioncompositions.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 2-component compositioncomprising a first component comprising at least one uracil of theformula I, a solid or liquid carrier and/or one or more surfactants anda second component comprising at least one further active compoundselected from the active compounds of groups b1 to b15, a solid orliquid carrier and/or one or more surfactants, where additionally bothcomponents may also comprise further auxiliaries customary for cropprotection compositions.

In binary compositions comprising at least one compound of the formula Ias component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula Ias component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of theformula I as component A, at least one herbicide B and at least onesafener C, the relative parts by weight of the components A:B aregenerally in the range of from 1:1000 to 1000:1, preferably in the rangeof from 1:500 to 500:1, in particular in the range of from 1:250 to250:1 and particularly preferably in the range of from 1:75 to 75:1; theweight ratio of the components A:C is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1; and the weight ratio ofthe components B:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1. Preferably, the weight ratio of the components A+B tothe component C is in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1.

Particularly preferred herbicides B are the herbicides B as definedabove; in particular the herbicides B.1-B.143 listed below in table B:

TABLE B Herbicide B B.1 clethodim B.2 clodinafop-propargyl B.3cycloxydim B.4 cyhalofop-butyl B.5 fenoxaprop-P-ethyl B.6 metamifop B.7pinoxaden B.8 profoxydim B.9 sethoxydim B.10 tepraloxydim B.11tralkoxydim B.12 esprocarb B.13 ethofumesate B.14 molinate B.15prosulfocarb B.16 thiobencarb B.17 triallate B.18 bensulfuron-methylB.19 bispyribac-sodium B.20 cloransulam B.21 chlorsulfuron B.22clorimuron B.23 cyclosulfamuron B.24 diclosulam B.25 florasulam B.26flumetsulam B.27 flupyrsulfuron-methyl-sodium B.28 foramsulfuron B.29imazamox B.30 imazapic B.31 imazapyr B.32 imazaquin B.33 imazethapyrB.34 imazosulfuron B.35 iodosulfuron-methyl-sodium B.36 mesosulfuronB.37 metazosulfuron B.38 metsulfuron B.39 metosulam B.40 nicosulfuronB.41 penoxsulam B.42 propoxycarbazon-sodium B.43 pyrazosulfuron-ethylB.44 pyribenzoxim B.45 pyriftalid B.46 pyroxsulam B.47 rimsulfuron B.48sulfosulfuron B.49 thiencarbazone-methyl B.50 thifensulfuron B.51tribenuron B.52 tritosulfuron B.53 ametryne B.54 atrazine B.55 bentazonB.56 bromoxynil B.57 diuron B.58 fluometuron B.59 hexazinone B.60isoproturon B.61 linuron B.62 metamitron B.63 metribuzin B.64 propanilB.65 simazin B.66 terbuthylazine B.67 terbutryn B.68 paraquat-dichlorideB.69 acifluorfen B.70 butafenacil B.71 carfentrazone-ethyl B.72flumioxazin B.73 fomesafen B.74 oxadiargyl B.75 oxyfluorfen B.76saflufenacil B.77 sulfentrazone B.78 ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo- 1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyl- oxy]acetate (CAS 353292-31-6) B.793-[7-fluoro-3-oxo-4-(prop-2-yn- yl)-3,4-dihydro-2H-benzo[1,4]-oxazin-6-yl]-1,5-dimethyl-6-thioxo- [1,3,5]triazinan-2,4-dione B.801,5-dimethyl-6-thioxo-3-(2,2,7- trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]- oxazin-6-yl)-1,3,5-triazinane- 2,4-dioneB.81 2-(2,2,7-Trifluoro-3-oxo-4-prop- 2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7- tetrahydro-isoindole-1,3-dione B.82benzobicyclon B.83 clomazone B.84 diflufenican B.85 flurochloridone B.86isoxaflutole B.87 mesotrione B.88 norflurazone B.89 picolinafen B.90sulcotrione B.91 tefuryltrione B.92 tembotrione B.93 topramezone B.94bicyclopyrone B.95 amitrole B.96 fluometuron B.97 glyphosate B.98glyphosate-isopropylammonium B.99 glyphosate-trimesium (sulfosate) B.100glufosinate B.101 glufosinate-P B.102 glufosinate-ammonium B.103pendimethalin B.104 trifluralin B.105 acetochlor B.106 butachlor B.107cafenstrole B.108 dimethenamid-P B.109 fentrazamide B.110 flufenacetB.111 mefenacet B.112 metazachlor B.113 metolachlor B.114 S-metolachlorB.115 pretilachlor B.116 fenoxasulfone B.117 isoxaben B.118pyroxasulfone B.119 2,4-D B.120 aminopyralid B.121 clopyralid B.122dicamba B.123 fluroxypyr-meptyl B.124 MCPA B.125 quinclorac B.126quinmerac B.127 aminocyclopyrachlor B.128 diflufenzopyr B.129diflufenzopyr-sodium B.130 dymron B.131 indanofan B.132 indaziflam B.133oxaziclomefone B.134 triaziflam B.135 II.1 B.136 II.2 B.137 II.3 B.138II.4 B.139 II.5 B.140 II.6 B.141 II.7 B.142 II.8 B.143 II.9

Particularly preferred safeners C, which, as component C, areconstituent of the composition according to the invention are thesafeners C as defined above; in particular the safeners C.1-C.12 listedbelow in table C:

TABLE C Safener C C.1 benoxacor C.2 cloquintocet C.3 cyprosulfamide C.4dichlormid C.5 fenchlorazole C.6 fenclorim C.7 furilazole C.8 isoxadifenC.9 mefenpyr C.10 naphthalic acid anhydride C.114-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3)C.12 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4)

The weight ratios of the individual components in the preferred mixturesmentioned below are within the limits given above, in particular withinthe preferred limits.

Particularly preferred are the compositions mentioned below comprisingthe uracils of formula I as defined and the substance(s) as defined inthe respective row of table 1;

especially preferred comprising as only herbicidal active compounds theuracils of formula I as defined and the substance(s) as defined in therespective row of table 1;

most preferably comprising as only active compounds the uracils offormula I as defined and the substance(s) as defined in the respectiverow of table 1.

Particularly preferred are compositions 1.1 to 1.1871 comprising theuracil Ia48 and the substance(s) as defined in the respective row oftable 1:

TABLE 1 (compositions 1.1 to 1.1871): comp. no. herbicide B safener C1.1 B.1 — 1.2 B.2 — 1.3 B.3 — 1.4 B.4 — 1.5 B.5 — 1.6 B.6 — 1.7 B.7 —1.8 B.8 — 1.9 B.9 — 1.10 B.10 — 1.11 B.11 — 1.12 B.12 — 1.13 B.13 — 1.14B.14 — 1.15 B.15 — 1.16 B.16 — 1.17 B.17 — 1.18 B.18 — 1.19 B.19 — 1.20B.20 — 1.21 B.21 — 1.22 B.22 — 1.23 B.23 — 1.24 B.24 — 1.25 B.25 — 1.26B.26 — 1.27 B.27 — 1.28 B.28 — 1.29 B.29 — 1.30 B.30 — 1.31 B.31 — 1.32B.32 — 1.33 B.33 — 1.34 B.34 — 1.35 B.35 — 1.36 B.36 — 1.37 B.37 — 1.38B.38 — 1.39 B.39 — 1.40 B.40 — 1.41 B.41 — 1.42 B.42 — 1.43 B.43 — 1.44B.44 — 1.45 B.45 — 1.46 B.46 — 1.47 B.47 — 1.48 B.48 — 1.49 B.49 — 1.50B.50 — 1.51 B.51 — 1.52 B.52 — 1.53 B.53 — 1.54 B.54 — 1.55 B.55 — 1.56B.56 — 1.57 B.57 — 1.58 B.58. — 1.59 B.59 — 1.60 B.60 — 1.61 B.61 — 1.62B.62 — 1.63 B.63 — 1.64 B.64 — 1.65 B.65 — 1.66 B.66 — 1.67 B.67 — 1.68B.68 — 1.69 B.69 — 1.70 B.70 — 1.71 B.71 — 1.72 B.72 — 1.73 B.73 — 1.74B.74 — 1.75 B.75 — 1.76 B.76 — 1.77 B.77 — 1.78 B.78 — 1.79 B.79 — 1.80B.80 — 1.81 B.81 — 1.82 B.82 — 1.83 B.83 — 1.84 B.84 — 1.85 B.85 — 1.86B.86 — 1.87 B.87 — 1.88 B.88 — 1.89 B.89 — 1.90 B.90 — 1.91 B.91 — 1.92B.92 — 1.93 B.93 — 1.94 B.94 — 1.95 B.95 — 1.96 B.96 — 1.97 B.97 — 1.98B.98 — 1.99 B.99 — 1.100 B.100 — 1.101 B.101 — 1.102 B.102 — 1.103 B.103— 1.104 B.104 — 1.105 B.105 — 1.106 B.106 — 1.107 B.107 — 1.108 B.108 —1.109 B.109 — 1.110 B.110 — 1.111 B.111 — 1.112 B.112 — 1.113 B.113 —1.114 B.114 — 1.115 B.115 — 1.116 B.116 — 1.117 B.117 — 1.118 B.118 —1.119 B.119 — 1.120 B.120 — 1.121 B.121 — 1.122 B.122 — 1.123 B.123 —1.124 B.124 — 1.125 B.125 — 1.126 B.126 — 1.127 B.127 — 1.128 B.128 —1.129 B.129 — 1.130 B.130 — 1.131 B.131 — 1.132 B.132 — 1.133 B.133 —1.134 B.134 — 1.135 B.135 — 1.136 B.136 — 1.137 B.137 — 1.138 B.138 —1.139 B.139 — 1.140 B.140 — 1.141 B.141 — 1.142 B.142 — 1.143 B.143 —1.144 B.1 C.1 1.145 B.2 C.1 1.146 B.3 C.1 1.147 B.4 C.1 1.148 B.5 C.11.149 B.6 C.1 1.150 B.7 C.1 1.151 B.8 C.1 1.152 B.9 C.1 1.153 B.10 C.11.154 B.11 C.1 1.155 B.12 C.1 1.156 B.13 C.1 1.157 B.14 C.1 1.158 B.15C.1 1.159 B.16 C.1 1.160 B.17 C.1 1.161 B.18 C.1 1.162 B.19 C.1 1.163B.20 C.1 1.164 B.21 C.1 1.165 B.22 C.1 1.166 B.23 C.1 1.167 B.24 C.11.168 B.25 C.1 1.169 B.26 C.1 1.170 B.27 C.1 1.171 B.28 C.1 1.172 B.29C.1 1.173 B.30 C.1 1.174 B.31 C.1 1.175 B.32 C.1 1.176 B.33 C.1 1.177B.34 C.1 1.178 B.35 C.1 1.179 B.36 C.1 1.180 B.37 C.1 1.181 B.38 C.11.182 B.39 C.1 1.183 B.40 C.1 1.184 B.41 C.1 1.185 B.42 C.1 1.186 B.43C.1 1.187 B.44 C.1 1.188 B.45 C.1 1.189 B.46 C.1 1.190 B.47 C.1 1.191B.48 C.1 1.192 B.49 C.1 1.193 B.50 C.1 1.194 B.51 C.1 1.195 B.52 C.11.196 B.53 C.1 1.197 B.54 C.1 1.198 B.55 C.1 1.199 B.56 C.1 1.200 B.57C.1 1.201 B.58. C.1 1.202 B.59 C.1 1.203 B.60 C.1 1.204 B.61 C.1 1.205B.62 C.1 1.206 B.63 C.1 1.207 B.64 C.1 1.208 B.65 C.1 1.209 B.66 C.11.210 B.67 C.1 1.211 B.68 C.1 1.212 B.69 C.1 1.213 B.70 C.1 1.214 B.71C.1 1.215 B.72 C.1 1.216 B.73 C.1 1.217 B.74 C.1 1.218 B.75 C.1 1.219B.76 C.1 1.220 B.77 C.1 1.221 B.78 C.1 1.222 B.79 C.1 1.223 B.80 C.11.224 B.81 C.1 1.225 B.82 C.1 1.226 B.83 C.1 1.227 B.84 C.1 1.228 B.85C.1 1.229 B.86 C.1 1.230 B.87 C.1 1.231 B.88 C.1 1.232 B.89 C.1 1.233B.90 C.1 1.234 B.91 C.1 1.235 B.92 C.1 1.236 B.93 C.1 1.237 B.94 C.11.238 B.95 C.1 1.239 B.96 C.1 1.240 B.97 C.1 1.241 B.98 C.1 1.242 B.99C.1 1.243 B.100 C.1 1.244 B.101 C.1 1.245 B.102 C.1 1.246 B.103 C.11.247 B.104 C.1 1.248 B.105 C.1 1.249 B.106 C.1 1.250 B.107 C.1 1.251B.108 C.1 1.252 B.109 C.1 1.253 B.110 C.1 1.254 B.111 C.1 1.255 B.112C.1 1.256 B.113 C.1 1.257 B.114 C.1 1.258 B.115 C.1 1.259 B.116 C.11.260 B.117 C.1 1.261 B.118 C.1 1.262 B.119 C.1 1.263 B.120 C.1 1.264B.121 C.1 1.265 B.122 C.1 1.266 B.123 C.1 1.267 B.124 C.1 1.268 B.125C.1 1.269 B.126 C.1 1.270 B.127 C.1 1.271 B.128 C.1 1.272 B.129 C.11.273 B.130 C.1 1.274 B.131 C.1 1.275 B.132 C.1 1.276 B.133 C.1 1.277B.134 C.1 1.278 B.135 C.1 1.279 B.136 C.1 1.280 B.137 C.1 1.281 B.138C.1 1.282 B.139 C.1 1.283 B.140 C.1 1.284 B.141 C.1 1.285 B.142 C.11.286 B.143 C.1 1.287 B.1 C.2 1.288 B.2 C.2 1.289 B.3 C.2 1.290 B.4 C.21.291 B.5 C.2 1.292 B.6 C.2 1.293 B.7 C.2 1.294 B.8 C.2 1.295 B.9 C.21.296 B.10 C.2 1.297 B.11 C.2 1.298 B.12 C.2 1.299 B.13 C.2 1.300 B.14C.2 1.301 B.15 C.2 1.302 B.16 C.2 1.303 B.17 C.2 1.304 B.18 C.2 1.305B.19 C.2 1.306 B.20 C.2 1.307 B.21 C.2 1.308 B.22 C.2 1.309 B.23 C.21.310 B.24 C.2 1.311 B.25 C.2 1.312 B.26 C.2 1.313 B.27 C.2 1.314 B.28C.2 1.315 B.29 C.2 1.316 B.30 C.2 1.317 B.31 C.2 1.318 B.32 C.2 1.319B.33 C.2 1.320 B.34 C.2 1.321 B.35 C.2 1.322 B.36 C.2 1.323 B.37 C.21.324 B.38 C.2 1.325 B.39 C.2 1.326 B.40 C.2 1.327 B.41 C.2 1.328 B.42C.2 1.329 B.43 C.2 1.330 B.44 C.2 1.331 B.45 C.2 1.332 B.46 C.2 1.333B.47 C.2 1.334 B.48 C.2 1.335 B.49 C.2 1.336 B.50 C.2 1.337 B.51 C.21.338 B.52 C.2 1.339 B.53 C.2 1.340 B.54 C.2 1.341 B.55 C.2 1.342 B.56C.2 1.343 B.57 C.2 1.344 B.58. C.2 1.345 B.59 C.2 1.346 B.60 C.2 1.347B.61 C.2 1.348 B.62 C.2 1.349 B.63 C.2 1.350 B.64 C.2 1.351 B.65 C.21.352 B.66 C.2 1.353 B.67 C.2 1.354 B.68 C.2 1.355 B.69 C.2 1.356 B.70C.2 1.357 B.71 C.2 1.358 B.72 C.2 1.359 B.73 C.2 1.360 B.74 C.2 1.361B.75 C.2 1.362 B.76 C.2 1.363 B.77 C.2 1.364 B.78 C.2 1.365 B.79 C.21.366 B.80 C.2 1.367 B.81 C.2 1.368 B.82 C.2 1.369 B.83 C.2 1.370 B.84C.2 1.371 B.85 C.2 1.372 B.86 C.2 1.373 B.87 C.2 1.374 B.88 C.2 1.375B.89 C.2 1.376 B.90 C.2 1.377 B.91 C.2 1.378 B.92 C.2 1.379 B.93 C.21.380 B.94 C.2 1.381 B.95 C.2 1.382 B.96 C.2 1.383 B.97 C.2 1.384 B.98C.2 1.385 B.99 C.2 1.386 B.100 C.2 1.387 B.101 C.2 1.388 B.102 C.2 1.389B.103 C.2 1.390 B.104 C.2 1.391 B.105 C.2 1.392 B.106 C.2 1.393 B.107C.2 1.394 B.108 C.2 1.395 B.109 C.2 1.396 B.110 C.2 1.397 B.111 C.21.398 B.112 C.2 1.399 B.113 C.2 1.400 B.114 C.2 1.401 B.115 C.2 1.402B.116 C.2 1.403 B.117 C.2 1.404 B.118 C.2 1.405 B.119 C.2 1.406 B.120C.2 1.407 B.121 C.2 1.408 B.122 C.2 1.409 B.123 C.2 1.410 B.124 C.21.411 B.125 C.2 1.412 B.126 C.2 1.413 B.127 C.2 1.414 B.128 C.2 1.415B.129 C.2 1.416 B.130 C.2 1.417 B.131 C.2 1.418 B.132 C.2 1.419 B.133C.2 1.420 B.134 C.2 1.421 B.135 C.2 1.422 B.136 C.2 1.423 B.137 C.21.424 B.138 C.2 1.425 B.139 C.2 1.426 B.140 C.2 1.427 B.141 C.2 1.428B.142 C.2 1.429 B.143 C.2 1.430 B.1 C.3 1.431 B.2 C.3 1.432 B.3 C.31.433 B.4 C.3 1.434 B.5 C.3 1.435 B.6 C.3 1.436 B.7 C.3 1.437 B.8 C.31.438 B.9 C.3 1.439 B.10 C.3 1.440 B.11 C.3 1.441 B.12 C.3 1.442 B.13C.3 1.443 B.14 C.3 1.444 B.15 C.3 1.445 B.16 C.3 1.446 B.17 C.3 1.447B.18 C.3 1.448 B.19 C.3 1.449 B.20 C.3 1.450 B.21 C.3 1.451 B.22 C.31.452 B.23 C.3 1.453 B.24 C.3 1.454 B.25 C.3 1.455 B.26 C.3 1.456 B.27C.3 1.457 B.28 C.3 1.458 B.29 C.3 1.459 B.30 C.3 1.460 B.31 C.3 1.461B.32 C.3 1.462 B.33 C.3 1.463 B.34 C.3 1.464 B.35 C.3 1.465 B.36 C.31.466 B.37 C.3 1.467 B.38 C.3 1.468 B.39 C.3 1.469 B.40 C.3 1.470 B.41C.3 1.471 B.42 C.3 1.472 B.43 C.3 1.473 B.44 C.3 1.474 B.45 C.3 1.475B.46 C.3 1.476 B.47 C.3 1.477 B.48 C.3 1.478 B.49 C.3 1.479 B.50 C.31.480 B.51 C.3 1.481 B.52 C.3 1.482 B.53 C.3 1.483 B.54 C.3 1.484 B.55C.3 1.485 B.56 C.3 1.486 B.57 C.3 1.487 B.58. C.3 1.488 B.59 C.3 1.489B.60 C.3 1.490 B.61 C.3 1.491 B.62 C.3 1.492 B.63 C.3 1.493 B.64 C.31.494 B.65 C.3 1.495 B.66 C.3 1.496 B.67 C.3 1.497 B.68 C.3 1.498 B.69C.3 1.499 B.70 C.3 1.500 B.71 C.3 1.501 B.72 C.3 1.502 B.73 C.3 1.503B.74 C.3 1.504 B.75 C.3 1.505 B.76 C.3 1.506 B.77 C.3 1.507 B.78 C.31.508 B.79 C.3 1.509 B.80 C.3 1.510 B.81 C.3 1.511 B.82 C.3 1.512 B.83C.3 1.513 B.84 C.3 1.514 B.85 C.3 1.515 B.86 C.3 1.516 B.87 C.3 1.517B.88 C.3 1.518 B.89 C.3 1.519 B.90 C.3 1.520 B.91 C.3 1.521 B.92 C.31.522 B.93 C.3 1.523 B.94 C.3 1.524 B.95 C.3 1.525 B.96 C.3 1.526 B.97C.3 1.527 B.98 C.3 1.528 B.99 C.3 1.529 B.100 C.3 1.530 B.101 C.3 1.531B.102 C.3 1.532 B.103 C.3 1.533 B.104 C.3 1.534 B.105 C.3 1.535 B.106C.3 1.536 B.107 C.3 1.537 B.108 C.3 1.538 B.109 C.3 1.539 B.110 C.31.540 B.111 C.3 1.541 B.112 C.3 1.542 B.113 C.3 1.543 B.114 C.3 1.544B.115 C.3 1.545 B.116 C.3 1.546 B.117 C.3 1.547 B.118 C.3 1.548 B.119C.3 1.549 B.120 C.3 1.550 B.121 C.3 1.551 B.122 C.3 1.552 B.123 C.31.553 B.124 C.3 1.554 B.125 C.3 1.555 B.126 C.3 1.556 B.127 C.3 1.557B.128 C.3 1.558 B.129 C.3 1.559 B.130 C.3 1.560 B.131 C.3 1.561 B.132C.3 1.562 B.133 C.3 1.563 B.134 C.3 1.564 B.135 C.3 1.565 B.136 C.31.566 B.137 C.3 1.567 B.138 C.3 1.568 B.139 C.3 1.569 B.140 C.3 1.570B.141 C.3 1.571 B.142 C.3 1.572 B.143 C.3 1.573 B.1 C.4 1.574 B.2 C.41.575 B.3 C.4 1.576 B.4 C.4 1.577 B.5 C.4 1.578 B.6 C.4 1.579 B.7 C.41.580 B.8 C.4 1.581 B.9 C.4 1.582 B.10 C.4 1.583 B.11 C.4 1.584 B.12 C.41.585 B.13 C.4 1.586 B.14 C.4 1.587 B.15 C.4 1.588 B.16 C.4 1.589 B.17C.4 1.590 B.18 C.4 1.591 B.19 C.4 1.592 B.20 C.4 1.593 B.21 C.4 1.594B.22 C.4 1.595 B.23 C.4 1.596 B.24 C.4 1.597 B.25 C.4 1.598 B.26 C.41.599 B.27 C.4 1.600 B.28 C.4 1.601 B.29 C.4 1.602 B.30 C.4 1.603 B.31C.4 1.604 B.32 C.4 1.605 B.33 C.4 1.606 B.34 C.4 1.607 B.35 C.4 1.608B.36 C.4 1.609 B.37 C.4 1.610 B.38 C.4 1.611 B.39 C.4 1.612 B.40 C.41.613 B.41 C.4 1.614 B.42 C.4 1.615 B.43 C.4 1.616 B.44 C.4 1.617 B.45C.4 1.618 B.46 C.4 1.619 B.47 C.4 1.620 B.48 C.4 1.621 B.49 C.4 1.622B.50 C.4 1.623 B.51 C.4 1.624 B.52 C.4 1.625 B.53 C.4 1.626 B.54 C.41.627 B.55 C.4 1.628 B.56 C.4 1.629 B.57 C.4 1.630 B.58. C.4 1.631 B.59C.4 1.632 B.60 C.4 1.633 B.61 C.4 1.634 B.62 C.4 1.635 B.63 C.4 1.636B.64 C.4 1.637 B.65 C.4 1.638 B.66 C.4 1.639 B.67 C.4 1.640 B.68 C.41.641 B.69 C.4 1.642 B.70 C.4 1.643 B.71 C.4 1.644 B.72 C.4 1.645 B.73C.4 1.646 B.74 C.4 1.647 B.75 C.4 1.648 B.76 C.4 1.649 B.77 C.4 1.650B.78 C.4 1.651 B.79 C.4 1.652 B.80 C.4 1.653 B.81 C.4 1.654 B.82 C.41.655 B.83 C.4 1.656 B.84 C.4 1.657 B.85 C.4 1.658 B.86 C.4 1.659 B.87C.4 1.660 B.88 C.4 1.661 B.89 C.4 1.662 B.90 C.4 1.663 B.91 C.4 1.664B.92 C.4 1.665 B.93 C.4 1.666 B.94 C.4 1.667 B.95 C.4 1.668 B.96 C.41.669 B.97 C.4 1.670 B.98 C.4 1.671 B.99 C.4 1.672 B.100 C.4 1.673 B.101C.4 1.674 B.102 C.4 1.675 B.103 C.4 1.676 B.104 C.4 1.677 B.105 C.41.678 B.106 C.4 1.679 B.107 C.4 1.680 B.108 C.4 1.681 B.109 C.4 1.682B.110 C.4 1.683 B.111 C.4 1.684 B.112 C.4 1.685 B.113 C.4 1.686 B.114C.4 1.687 B.115 C.4 1.688 B.116 C.4 1.689 B.117 C.4 1.690 B.118 C.41.691 B.119 C.4 1.692 B.120 C.4 1.693 B.121 C.4 1.694 B.122 C.4 1.695B.123 C.4 1.696 B.124 C.4 1.697 B.125 C.4 1.698 B.126 C.4 1.699 B.127C.4 1.700 B.128 C.4 1.701 B.129 C.4 1.702 B.130 C.4 1.703 B.131 C.41.704 B.132 C.4 1.705 B.133 C.4 1.706 B.134 C.4 1.707 B.135 C.4 1.708B.136 C.4 1.709 B.137 C.4 1.710 B.138 C.4 1.711 B.139 C.4 1.712 B.140C.4 1.713 B.141 C.4 1.714 B.142 C.4 1.715 B.143 C.4 1.716 B.1 C.5 1.717B.2 C.5 1.718 B.3 C.5 1.719 B.4 C.5 1.720 B.5 C.5 1.721 B.6 C.5 1.722B.7 C.5 1.723 B.8 C.5 1.724 B.9 C.5 1.725 B.10 C.5 1.726 B.11 C.5 1.727B.12 C.5 1.728 B.13 C.5 1.729 B.14 C.5 1.730 B.15 C.5 1.731 B.16 C.51.732 B.17 C.5 1.733 B.18 C.5 1.734 B.19 C.5 1.735 B.20 C.5 1.736 B.21C.5 1.737 B.22 C.5 1.738 B.23 C.5 1.739 B.24 C.5 1.740 B.25 C.5 1.741B.26 C.5 1.742 B.27 C.5 1.743 B.28 C.5 1.744 B.29 C.5 1.745 B.30 C.51.746 B.31 C.5 1.747 B.32 C.5 1.748 B.33 C.5 1.749 B.34 C.5 1.750 B.35C.5 1.751 B.36 C.5 1.752 B.37 C.5 1.753 B.38 C.5 1.754 B.39 C.5 1.755B.40 C.5 1.756 B.41 C.5 1.757 B.42 C.5 1.758 B.43 C.5 1.759 B.44 C.51.760 B.45 C.5 1.761 B.46 C.5 1.762 B.47 C.5 1.763 B.48 C.5 1.764 B.49C.5 1.765 B.50 C.5 1.766 B.51 C.5 1.767 B.52 C.5 1.768 B.53 C.5 1.769B.54 C.5 1.770 B.55 C.5 1.771 B.56 C.5 1.772 B.57 C.5 1.773 B.58. C.51.774 B.59 C.5 1.775 B.60 C.5 1.776 B.61 C.5 1.777 B.62 C.5 1.778 B.63C.5 1.779 B.64 C.5 1.780 B.65 C.5 1.781 B.66 C.5 1.782 B.67 C.5 1.783B.68 C.5 1.784 B.69 C.5 1.785 B.70 C.5 1.786 B.71 C.5 1.787 B.72 C.51.788 B.73 C.5 1.789 B.74 C.5 1.790 B.75 C.5 1.791 B.76 C.5 1.792 B.77C.5 1.793 B.78 C.5 1.794 B.79 C.5 1.795 B.80 C.5 1.796 B.81 C.5 1.797B.82 C.5 1.798 B.83 C.5 1.799 B.84 C.5 1.800 B.85 C.5 1.801 B.86 C.51.802 B.87 C.5 1.803 B.88 C.5 1.804 B.89 C.5 1.805 B.90 C.5 1.806 B.91C.5 1.807 B.92 C.5 1.808 B.93 C.5 1.809 B.94 C.5 1.810 B.95 C.5 1.811B.96 C.5 1.812 B.97 C.5 1.813 B.98 C.5 1.814 B.99 C.5 1.815 B.100 C.51.816 B.101 C.5 1.817 B.102 C.5 1.818 B.103 C.5 1.819 B.104 C.5 1.820B.105 C.5 1.821 B.106 C.5 1.822 B.107 C.5 1.823 B.108 C.5 1.824 B.109C.5 1.825 B.110 C.5 1.826 B.111 C.5 1.827 B.112 C.5 1.828 B.113 C.51.829 B.114 C.5 1.830 B.115 C.5 1.831 B.116 C.5 1.832 B.117 C.5 1.833B.118 C.5 1.834 B.119 C.5 1.835 B.120 C.5 1.836 B.121 C.5 1.837 B.122C.5 1.838 B.123 C.5 1.839 B.124 C.5 1.840 B.125 C.5 1.841 B.126 C.51.842 B.127 C.5 1.843 B.128 C.5 1.844 B.129 C.5 1.845 B.130 C.5 1.846B.131 C.5 1.847 B.132 C.5 1.848 B.133 C.5 1.849 B.134 C.5 1.850 B.135C.5 1.851 B.136 C.5 1.852 B.137 C.5 1.853 B.138 C.5 1.854 B.139 C.51.855 B.140 C.5 1.856 B.141 C.5 1.857 B.142 C.5 1.858 B.143 C.5 1.859B.1 C.6 1.860 B.2 C.6 1.861 B.3 C.6 1.862 B.4 C.6 1.863 B.5 C.6 1.864B.6 C.6 1.865 B.7 C.6 1.866 B.8 C.6 1.867 B.9 C.6 1.868 B.10 C.6 1.869B.11 C.6 1.870 B.12 C.6 1.871 B.13 C.6 1.872 B.14 C.6 1.873 B.15 C.61.874 B.16 C.6 1.875 B.17 C.6 1.876 B.18 C.6 1.877 B.19 C.6 1.878 B.20C.6 1.879 B.21 C.6 1.880 B.22 C.6 1.881 B.23 C.6 1.882 B.24 C.6 1.883B.25 C.6 1.884 B.26 C.6 1.885 B.27 C.6 1.886 B.28 C.6 1.887 B.29 C.61.888 B.30 C.6 1.889 B.31 C.6 1.890 B.32 C.6 1.891 B.33 C.6 1.892 B.34C.6 1.893 B.35 C.6 1.894 B.36 C.6 1.895 B.37 C.6 1.896 B.38 C.6 1.897B.39 C.6 1.898 B.40 C.6 1.899 B.41 C.6 1.900 B.42 C.6 1.901 B.43 C.61.902 B.44 C.6 1.903 B.45 C.6 1.904 B.46 C.6 1.905 B.47 C.6 1.906 B.48C.6 1.907 B.49 C.6 1.908 B.50 C.6 1.909 B.51 C.6 1.910 B.52 C.6 1.911B.53 C.6 1.912 B.54 C.6 1.913 B.55 C.6 1.914 B.56 C.6 1.915 B.57 C.61.916 B.58. C.6 1.917 B.59 C.6 1.918 B.60 C.6 1.919 B.61 C.6 1.920 B.62C.6 1.921 B.63 C.6 1.922 B.64 C.6 1.923 B.65 C.6 1.924 B.66 C.6 1.925B.67 C.6 1.926 B.68 C.6 1.927 B.69 C.6 1.928 B.70 C.6 1.929 B.71 C.61.930 B.72 C.6 1.931 B.73 C.6 1.932 B.74 C.6 1.933 B.75 C.6 1.934 B.76C.6 1.935 B.77 C.6 1.936 B.78 C.6 1.937 B.79 C.6 1.938 B.80 C.6 1.939B.81 C.6 1.940 B.82 C.6 1.941 B.83 C.6 1.942 B.84 C.6 1.943 B.85 C.61.944 B.86 C.6 1.945 B.87 C.6 1.946 B.88 C.6 1.947 B.89 C.6 1.948 B.90C.6 1.949 B.91 C.6 1.950 B.92 C.6 1.951 B.93 C.6 1.952 B.94 C.6 1.953B.95 C.6 1.954 B.96 C.6 1.955 B.97 C.6 1.956 B.98 C.6 1.957 B.99 C.61.958 B.100 C.6 1.959 B.101 C.6 1.960 B.102 C.6 1.961 B.103 C.6 1.962B.104 C.6 1.963 B.105 C.6 1.964 B.106 C.6 1.965 B.107 C.6 1.966 B.108C.6 1.967 B.109 C.6 1.968 B.110 C.6 1.969 B.111 C.6 1.970 B.112 C.61.971 B.113 C.6 1.972 B.114 C.6 1.973 B.115 C.6 1.974 B.116 C.6 1.975B.117 C.6 1.976 B.118 C.6 1.977 B.119 C.6 1.978 B.120 C.6 1.979 B.121C.6 1.980 B.122 C.6 1.981 B.123 C.6 1.982 B.124 C.6 1.983 B.125 C.61.984 B.126 C.6 1.985 B.127 C.6 1.986 B.128 C.6 1.987 B.129 C.6 1.988B.130 C.6 1.989 B.131 C.6 1.990 B.132 C.6 1.991 B.133 C.6 1.992 B.134C.6 1.993 B.135 C.6 1.994 B.136 C.6 1.995 B.137 C.6 1.996 B.138 C.61.997 B.139 C.6 1.998 B.140 C.6 1.999 B.141 C.6 1.1000 B.142 C.6 1.1001B.143 C.6 1.1002 B.1 C.7 1.1003 B.2 C.7 1.1004 B.3 C.7 1.1005 B.4 C.71.1006 B.5 C.7 1.1007 B.6 C.7 1.1008 B.7 C.7 1.1009 B.8 C.7 1.1010 B.9C.7 1.1011 B.10 C.7 1.1012 B.11 C.7 1.1013 B.12 C.7 1.1014 B.13 C.71.1015 B.14 C.7 1.1016 B.15 C.7 1.1017 B.16 C.7 1.1018 B.17 C.7 1.1019B.18 C.7 1.1020 B.19 C.7 1.1021 B.20 C.7 1.1022 B.21 C.7 1.1023 B.22 C.71.1024 B.23 C.7 1.1025 B.24 C.7 1.1026 B.25 C.7 1.1027 B.26 C.7 1.1028B.27 C.7 1.1029 B.28 C.7 1.1030 B.29 C.7 1.1031 B.30 C.7 1.1032 B.31 C.71.1033 B.32 C.7 1.1034 B.33 C.7 1.1035 B.34 C.7 1.1036 B.35 C.7 1.1037B.36 C.7 1.1038 B.37 C.7 1.1039 B.38 C.7 1.1040 B.39 C.7 1.1041 B.40 C.71.1042 B.41 C.7 1.1043 B.42 C.7 1.1044 B.43 C.7 1.1045 B.44 C.7 1.1046B.45 C.7 1.1047 B.46 C.7 1.1048 B.47 C.7 1.1049 B.48 C.7 1.1050 B.49 C.71.1051 B.50 C.7 1.1052 B.51 C.7 1.1053 B.52 C.7 1.1054 B.53 C.7 1.1055B.54 C.7 1.1056 B.55 C.7 1.1057 B.56 C.7 1.1058 B.57 C.7 1.1059 B.58.C.7 1.1060 B.59 C.7 1.1061 B.60 C.7 1.1062 B.61 C.7 1.1063 B.62 C.71.1064 B.63 C.7 1.1065 B.64 C.7 1.1066 B.65 C.7 1.1067 B.66 C.7 1.1068B.67 C.7 1.1069 B.68 C.7 1.1070 B.69 C.7 1.1071 B.70 C.7 1.1072 B.71 C.71.1073 B.72 C.7 1.1074 B.73 C.7 1.1075 B.74 C.7 1.1076 B.75 C.7 1.1077B.76 C.7 1.1078 B.77 C.7 1.1079 B.78 C.7 1.1080 B.79 C.7 1.1081 B.80 C.71.1082 B.81 C.7 1.1083 B.82 C.7 1.1084 B.83 C.7 1.1085 B.84 C.7 1.1086B.85 C.7 1.1087 B.86 C.7 1.1088 B.87 C.7 1.1089 B.88 C.7 1.1090 B.89 C.71.1091 B.90 C.7 1.1092 B.91 C.7 1.1093 B.92 C.7 1.1094 B.93 C.7 1.1095B.94 C.7 1.1096 B.95 C.7 1.1097 B.96 C.7 1.1098 B.97 C.7 1.1099 B.98 C.71.1100 B.99 C.7 1.1101 B.100 C.7 1.1102 B.101 C.7 1.1103 B.102 C.71.1104 B.103 C.7 1.1105 B.104 C.7 1.1106 B.105 C.7 1.1107 B.106 C.71.1108 B.107 C.7 1.1109 B.108 C.7 1.1110 B.109 C.7 1.1111 B.110 C.71.1112 B.111 C.7 1.1113 B.112 C.7 1.1114 B.113 C.7 1.1115 B.114 C.71.1116 B.115 C.7 1.1117 B.116 C.7 1.1118 B.117 C.7 1.1119 B.118 C.71.1120 B.119 C.7 1.1121 B.120 C.7 1.1122 B.121 C.7 1.1123 B.122 C.71.1124 B.123 C.7 1.1125 B.124 C.7 1.1126 B.125 C.7 1.1127 B.126 C.71.1128 B.127 C.7 1.1129 B.128 C.7 1.1130 B.129 C.7 1.1131 B.130 C.71.1132 B.131 C.7 1.1133 B.132 C.7 1.1134 B.133 C.7 1.1135 B.134 C.71.1136 B.135 C.7 1.1137 B.136 C.7 1.1138 B.137 C.7 1.1139 B.138 C.71.1140 B.139 C.7 1.1141 B.140 C.7 1.1142 B.141 C.7 1.1143 B.142 C.71.1144 B.143 C.7 1.1145 B.1 C.8 1.1146 B.2 C.8 1.1147 B.3 C.8 1.1148 B.4C.8 1.1149 B.5 C.8 1.1150 B.6 C.8 1.1151 B.7 C.8 1.1152 B.8 C.8 1.1153B.9 C.8 1.1154 B.10 C.8 1.1155 B.11 C.8 1.1156 B.12 C.8 1.1157 B.13 C.81.1158 B.14 C.8 1.1159 B.15 C.8 1.1160 B.16 C.8 1.1161 B.17 C.8 1.1162B.18 C.8 1.1163 B.19 C.8 1.1164 B.20 C.8 1.1165 B.21 C.8 1.1166 B.22 C.81.1167 B.23 C.8 1.1168 B.24 C.8 1.1169 B.25 C.8 1.1170 B.26 C.8 1.1171B.27 C.8 1.1172 B.28 C.8 1.1173 B.29 C.8 1.1174 B.30 C.8 1.1175 B.31 C.81.1176 B.32 C.8 1.1177 B.33 C.8 1.1178 B.34 C.8 1.1179 B.35 C.8 1.1180B.36 C.8 1.1181 B.37 C.8 1.1182 B.38 C.8 1.1183 B.39 C.8 1.1184 B.40 C.81.1185 B.41 C.8 1.1186 B.42 C.8 1.1187 B.43 C.8 1.1188 B.44 C.8 1.1189B.45 C.8 1.1190 B.46 C.8 1.1191 B.47 C.8 1.1192 B.48 C.8 1.1193 B.49 C.81.1194 B.50 C.8 1.1195 B.51 C.8 1.1196 B.52 C.8 1.1197 B.53 C.8 1.1198B.54 C.8 1.1199 B.55 C.8 1.1200 B.56 C.8 1.1201 B.57 C.8 1.1202 B.58.C.8 1.1203 B.59 C.8 1.1204 B.60 C.8 1.1205 B.61 C.8 1.1206 B.62 C.81.1207 B.63 C.8 1.1208 B.64 C.8 1.1209 B.65 C.8 1.1210 B.66 C.8 1.1211B.67 C.8 1.1212 B.68 C.8 1.1213 B.69 C.8 1.1214 B.70 C.8 1.1215 B.71 C.81.1216 B.72 C.8 1.1217 B.73 C.8 1.1218 B.74 C.8 1.1219 B.75 C.8 1.1220B.76 C.8 1.1221 B.77 C.8 1.1222 B.78 C.8 1.1223 B.79 C.8 1.1224 B.80 C.81.1225 B.81 C.8 1.1226 B.82 C.8 1.1227 B.83 C.8 1.1228 B.84 C.8 1.1229B.85 C.8 1.1230 B.86 C.8 1.1231 B.87 C.8 1.1232 B.88 C.8 1.1233 B.89 C.81.1234 B.90 C.8 1.1235 B.91 C.8 1.1236 B.92 C.8 1.1237 B.93 C.8 1.1238B.94 C.8 1.1239 B.95 C.8 1.1240 B.96 C.8 1.1241 B.97 C.8 1.1242 B.98 C.81.1243 B.99 C.8 1.1244 B.100 C.8 1.1245 B.101 C.8 1.1246 B.102 C.81.1247 B.103 C.8 1.1248 B.104 C.8 1.1249 B.105 C.8 1.1250 B.106 C.81.1251 B.107 C.8 1.1252 B.108 C.8 1.1253 B.109 C.8 1.1254 B.110 C.81.1255 B.111 C.8 1.1256 B.112 C.8 1.1257 B.113 C.8 1.1258 B.114 C.81.1259 B.115 C.8 1.1260 B.116 C.8 1.1261 B.117 C.8 1.1262 B.118 C.81.1263 B.119 C.8 1.1264 B.120 C.8 1.1265 B.121 C.8 1.1266 B.122 C.81.1267 B.123 C.8 1.1268 B.124 C.8 1.1269 B.125 C.8 1.1270 B.126 C.81.1271 B.127 C.8 1.1272 B.128 C.8 1.1273 B.129 C.8 1.1274 B.130 C.81.1275 B.131 C.8 1.1276 B.132 C.8 1.1277 B.133 C.8 1.1278 B.134 C.81.1279 B.135 C.8 1.1280 B.136 C.8 1.1281 B.137 C.8 1.1282 B.138 C.81.1283 B.139 C.8 1.1284 B.140 C.8 1.1285 B.141 C.8 1.1286 B.142 C.81.1287 B.143 C.8 1.1288 B.1 C.9 1.1289 B.2 C.9 1.1290 B.3 C.9 1.1291 B.4C.9 1.1292 B.5 C.9 1.1293 B.6 C.9 1.1294 B.7 C.9 1.1295 B.8 C.9 1.1296B.9 C.9 1.1297 B.10 C.9 1.1298 B.11 C.9 1.1299 B.12 C.9 1.1300 B.13 C.91.1301 B.14 C.9 1.1302 B.15 C.9 1.1303 B.16 C.9 1.1304 B.17 C.9 1.1305B.18 C.9 1.1306 B.19 C.9 1.1307 B.20 C.9 1.1308 B.21 C.9 1.1309 B.22 C.91.1310 B.23 C.9 1.1311 B.24 C.9 1.1312 B.25 C.9 1.1313 B.26 C.9 1.1314B.27 C.9 1.1315 B.28 C.9 1.1316 B.29 C.9 1.1317 B.30 C.9 1.1318 B.31 C.91.1319 B.32 C.9 1.1320 B.33 C.9 1.1321 B.34 C.9 1.1322 B.35 C.9 1.1323B.36 C.9 1.1324 B.37 C.9 1.1325 B.38 C.9 1.1326 B.39 C.9 1.1327 B.40 C.91.1328 B.41 C.9 1.1329 B.42 C.9 1.1330 B.43 C.9 1.1331 B.44 C.9 1.1332B.45 C.9 1.1333 B.46 C.9 1.1334 B.47 C.9 1.1335 B.48 C.9 1.1336 B.49 C.91.1337 B.50 C.9 1.1338 B.51 C.9 1.1339 B.52 C.9 1.1340 B.53 C.9 1.1341B.54 C.9 1.1342 B.55 C.9 1.1343 B.56 C.9 1.1344 B.57 C.9 1.1345 B.58.C.9 1.1346 B.59 C.9 1.1347 B.60 C.9 1.1348 B.61 C.9 1.1349 B.62 C.91.1350 B.63 C.9 1.1351 B.64 C.9 1.1352 B.65 C.9 1.1353 B.66 C.9 1.1354B.67 C.9 1.1355 B.68 C.9 1.1356 B.69 C.9 1.1357 B.70 C.9 1.1358 B.71 C.91.1359 B.72 C.9 1.1360 B.73 C.9 1.1361 B.74 C.9 1.1362 B.75 C.9 1.1363B.76 C.9 1.1364 B.77 C.9 1.1365 B.78 C.9 1.1366 B.79 C.9 1.1367 B.80 C.91.1368 B.81 C.9 1.1369 B.82 C.9 1.1370 B.83 C.9 1.1371 B.84 C.9 1.1372B.85 C.9 1.1373 B.86 C.9 1.1374 B.87 C.9 1.1375 B.88 C.9 1.1376 B.89 C.91.1377 B.90 C.9 1.1378 B.91 C.9 1.1379 B.92 C.9 1.1380 B.93 C.9 1.1381B.94 C.9 1.1382 B.95 C.9 1.1383 B.96 C.9 1.1384 B.97 C.9 1.1385 B.98 C.91.1386 B.99 C.9 1.1387 B.100 C.9 1.1388 B.101 C.9 1.1389 B.102 C.91.1390 B.103 C.9 1.1391 B.104 C.9 1.1392 B.105 C.9 1.1393 B.106 C.91.1394 B.107 C.9 1.1395 B.108 C.9 1.1396 B.109 C.9 1.1397 B.110 C.91.1398 B.111 C.9 1.1399 B.112 C.9 1.1400 B.113 C.9 1.1401 B.114 C.91.1402 B.115 C.9 1.1403 B.116 C.9 1.1404 B.117 C.9 1.1405 B.118 C.91.1406 B.119 C.9 1.1407 B.120 C.9 1.1408 B.121 C.9 1.1409 B.122 C.91.1410 B.123 C.9 1.1411 B.124 C.9 1.1412 B.125 C.9 1.1413 B.126 C.91.1414 B.127 C.9 1.1415 B.128 C.9 1.1416 B.129 C.9 1.1417 B.130 C.91.1418 B.131 C.9 1.1419 B.132 C.9 1.1420 B.133 C.9 1.1421 B.134 C.91.1422 B.135 C.9 1.1423 B.136 C.9 1.1424 B.137 C.9 1.1425 B.138 C.91.1426 B.139 C.9 1.1427 B.140 C.9 1.1428 B.141 C.9 1.1429 B.142 C.91.1430 B.143 C.9 1.1431 B.1 C.10 1.1432 B.2 C.10 1.1433 B.3 C.10 1.1434B.4 C.10 1.1435 B.5 C.10 1.1436 B.6 C.10 1.1437 B.7 C.10 1.1438 B.8 C.101.1439 B.9 C.10 1.1440 B.10 C.10 1.1441 B.11 C.10 1.1442 B.12 C.101.1443 B.13 C.10 1.1444 B.14 C.10 1.1445 B.15 C.10 1.1446 B.16 C.101.1447 B.17 C.10 1.1448 B.18 C.10 1.1449 B.19 C.10 1.1450 B.20 C.101.1451 B.21 C.10 1.1452 B.22 C.10 1.1453 B.23 C.10 1.1454 B.24 C.101.1455 B.25 C.10 1.1456 B.26 C.10 1.1457 B.27 C.10 1.1458 B.28 C.101.1459 B.29 C.10 1.1460 B.30 C.10 1.1461 B.31 C.10 1.1462 B.32 C.101.1463 B.33 C.10 1.1464 B.34 C.10 1.1465 B.35 C.10 1.1466 B.36 C.101.1467 B.37 C.10 1.1468 B.38 C.10 1.1469 B.39 C.10 1.1470 B.40 C.101.1471 B.41 C.10 1.1472 B.42 C.10 1.1473 B.43 C.10 1.1474 B.44 C.101.1475 B.45 C.10 1.1476 B.46 C.10 1.1477 B.47 C.10 1.1478 B.48 C.101.1479 B.49 C.10 1.1480 B.50 C.10 1.1481 B.51 C.10 1.1482 B.52 C.101.1483 B.53 C.10 1.1484 B.54 C.10 1.1485 B.55 C.10 1.1486 B.56 C.101.1487 B.57 C.10 1.1488 B.58. C.10 1.1489 B.59 C.10 1.1490 B.60 C.101.1491 B.61 C.10 1.1492 B.62 C.10 1.1493 B.63 C.10 1.1494 B.64 C.101.1495 B.65 C.10 1.1496 B.66 C.10 1.1497 B.67 C.10 1.1498 B.68 C.101.1499 B.69 C.10 1.1500 B.70 C.10 1.1501 B.71 C.10 1.1502 B.72 C.101.1503 B.73 C.10 1.1504 B.74 C.10 1.1505 B.75 C.10 1.1506 B.76 C.101.1507 B.77 C.10 1.1508 B.78 C.10 1.1509 B.79 C.10 1.1510 B.80 C.101.1511 B.81 C.10 1.1512 B.82 C.10 1.1513 B.83 C.10 1.1514 B.84 C.101.1515 B.85 C.10 1.1516 B.86 C.10 1.1517 B.87 C.10 1.1518 B.88 C.101.1519 B.89 C.10 1.1520 B.90 C.10 1.1521 B.91 C.10 1.1522 B.92 C.101.1523 B.93 C.10 1.1524 B.94 C.10 1.1525 B.95 C.10 1.1526 B.96 C.101.1527 B.97 C.10 1.1528 B.98 C.10 1.1529 B.99 C.10 1.1530 B.100 C.101.1531 B.101 C.10 1.1532 B.102 C.10 1.1533 B.103 C.10 1.1534 B.104 C.101.1535 B.105 C.10 1.1536 B.106 C.10 1.1537 B.107 C.10 1.1538 B.108 C.101.1539 B.109 C.10 1.1540 B.110 C.10 1.1541 B.111 C.10 1.1542 B.112 C.101.1543 B.113 C.10 1.1544 B.114 C.10 1.1545 B.115 C.10 1.1546 B.116 C.101.1547 B.117 C.10 1.1548 B.118 C.10 1.1549 B.119 C.10 1.1550 B.120 C.101.1551 B.121 C.10 1.1552 B.122 C.10 1.1553 B.123 C.10 1.1554 B.124 C.101.1555 B.125 C.10 1.1556 B.126 C.10 1.1557 B.127 C.10 1.1558 B.128 C.101.1559 B.129 C.10 1.1560 B.130 C.10 1.1561 B.131 C.10 1.1562 B.132 C.101.1563 B.133 C.10 1.1564 B.134 C.10 1.1565 B.135 C.10 1.1566 B.136 C.101.1567 B.137 C.10 1.1568 B.138 C.10 1.1569 B.139 C.10 1.1570 B.140 C.101.1571 B.141 C.10 1.1572 B.142 C.10 1.1573 B.143 C.10 1.1574 B.1 C.111.1575 B.2 C.11 1.1576 B.3 C.11 1.1577 B.4 C.11 1.1578 B.5 C.11 1.1579B.6 C.11 1.1580 B.7 C.11 1.1581 B.8 C.11 1.1582 B.9 C.11 1.1583 B.10C.11 1.1584 B.11 C.11 1.1585 B.12 C.11 1.1586 B.13 C.11 1.1587 B.14 C.111.1588 B.15 C.11 1.1589 B.16 C.11 1.1590 B.17 C.11 1.1591 B.18 C.111.1592 B.19 C.11 1.1593 B.20 C.11 1.1594 B.21 C.11 1.1595 B.22 C.111.1596 B.23 C.11 1.1597 B.24 C.11 1.1598 B.25 C.11 1.1599 B.26 C.111.1600 B.27 C.11 1.1601 B.28 C.11 1.1602 B.29 C.11 1.1603 B.30 C.111.1604 B.31 C.11 1.1605 B.32 C.11 1.1606 B.33 C.11 1.1607 B.34 C.111.1608 B.35 C.11 1.1609 B.36 C.11 1.1610 B.37 C.11 1.1611 B.38 C.111.1612 B.39 C.11 1.1613 B.40 C.11 1.1614 B.41 C.11 1.1615 B.42 C.111.1616 B.43 C.11 1.1617 B.44 C.11 1.1618 B.45 C.11 1.1619 B.46 C.111.1620 B.47 C.11 1.1621 B.48 C.11 1.1622 B.49 C.11 1.1623 B.50 C.111.1624 B.51 C.11 1.1625 B.52 C.11 1.1626 B.53 C.11 1.1627 B.54 C.111.1628 B.55 C.11 1.1629 B.56 C.11 1.1630 B.57 C.11 1.1631 B.58. C.111.1632 B.59 C.11 1.1633 B.60 C.11 1.1634 B.61 C.11 1.1635 B.62 C.111.1636 B.63 C.11 1.1637 B.64 C.11 1.1638 B.65 C.11 1.1639 B.66 C.111.1640 B.67 C.11 1.1641 B.68 C.11 1.1642 B.69 C.11 1.1643 B.70 C.111.1644 B.71 C.11 1.1645 B.72 C.11 1.1646 B.73 C.11 1.1647 B.74 C.111.1648 B.75 C.11 1.1649 B.76 C.11 1.1650 B.77 C.11 1.1651 B.78 C.111.1652 B.79 C.11 1.1653 B.80 C.11 1.1654 B.81 C.11 1.1655 B.82 C.111.1656 B.83 C.11 1.1657 B.84 C.11 1.1658 B.85 C.11 1.1659 B.86 C.111.1660 B.87 C.11 1.1661 B.88 C.11 1.1662 B.89 C.11 1.1663 B.90 C.111.1664 B.91 C.11 1.1665 B.92 C.11 1.1666 B.93 C.11 1.1667 B.94 C.111.1668 B.95 C.11 1.1669 B.96 C.11 1.1670 B.97 C.11 1.1671 B.98 C.111.1672 B.99 C.11 1.1673 B.100 C.11 1.1674 B.101 C.11 1.1675 B.102 C.111.1676 B.103 C.11 1.1677 B.104 C.11 1.1678 B.105 C.11 1.1679 B.106 C.111.1680 B.107 C.11 1.1681 B.108 C.11 1.1682 B.109 C.11 1.1683 B.110 C.111.1684 B.111 C.11 1.1685 B.112 C.11 1.1686 B.113 C.11 1.1687 B.114 C.111.1688 B.115 C.11 1.1689 B.116 C.11 1.1690 B.117 C.11 1.1691 B.118 C.111.1692 B.119 C.11 1.1693 B.120 C.11 1.1694 B.121 C.11 1.1695 B.122 C.111.1696 B.123 C.11 1.1697 B.124 C.11 1.1698 B.125 C.11 1.1699 B.126 C.111.1700 B.127 C.11 1.1701 B.128 C.11 1.1702 B.129 C.11 1.1703 B.130 C.111.1704 B.131 C.11 1.1705 B.132 C.11 1.1706 B.133 C.11 1.1707 B.134 C.111.1708 B.135 C.11 1.1709 B.136 C.11 1.1710 B.137 C.11 1.1711 B.138 C.111.1712 B.139 C.11 1.1713 B.140 C.11 1.1714 B.141 C.11 1.1715 B.142 C.111.1716 B.143 C.11 1.1717 B.1 C.12 1.1718 B.2 C.12 1.1719 B.3 C.12 1.1720B.4 C.12 1.1721 B.5 C.12 1.1722 B.6 C.12 1.1723 B.7 C.12 1.1724 B.8 C.121.1725 B.9 C.12 1.1726 B.10 C.12 1.1727 B.11 C.12 1.1728 B.12 C.121.1729 B.13 C.12 1.1730 B.14 C.12 1.1731 B.15 C.12 1.1732 B.16 C.121.1733 B.17 C.12 1.1734 B.18 C.12 1.1735 B.19 C.12 1.1736 B.20 C.121.1737 B.21 C.12 1.1738 B.22 C.12 1.1739 B.23 C.12 1.1740 B.24 C.121.1741 B.25 C.12 1.1742 B.26 C.12 1.1743 B.27 C.12 1.1744 B.28 C.121.1745 B.29 C.12 1.1746 B.30 C.12 1.1747 B.31 C.12 1.1748 B.32 C.121.1749 B.33 C.12 1.1750 B.34 C.12 1.1751 B.35 C.12 1.1752 B.36 C.121.1753 B.37 C.12 1.1754 B.38 C.12 1.1755 B.39 C.12 1.1756 B.40 C.121.1757 B.41 C.12 1.1758 B.42 C.12 1.1759 B.43 C.12 1.1760 B.44 C.121.1761 B.45 C.12 1.1762 B.46 C.12 1.1763 B.47 C.12 1.1764 B.48 C.121.1765 B.49 C.12 1.1766 B.50 C.12 1.1767 B.51 C.12 1.1768 B.52 C.121.1769 B.53 C.12 1.1770 B.54 C.12 1.1771 B.55 C.12 1.1772 B.56 C.121.1773 B.57 C.12 1.1774 B.58. C.12 1.1775 B.59 C.12 1.1776 B.60 C.121.1777 B.61 C.12 1.1778 B.62 C.12 1.1779 B.63 C.12 1.1780 B.64 C.121.1781 B.65 C.12 1.1782 B.66 C.12 1.1783 B.67 C.12 1.1784 B.68 C.121.1785 B.69 C.12 1.1786 B.70 C.12 1.1787 B.71 C.12 1.1788 B.72 C.121.1789 B.73 C.12 1.1790 B.74 C.12 1.1791 B.75 C.12 1.1792 B.76 C.121.1793 B.77 C.12 1.1794 B.78 C.12 1.1795 B.79 C.12 1.1796 B.80 C.121.1797 B.81 C.12 1.1798 B.82 C.12 1.1799 B.83 C.12 1.1800 B.84 C.121.1801 B.85 C.12 1.1802 B.86 C.12 1.1803 B.87 C.12 1.1804 B.88 C.121.1805 B.89 C.12 1.1806 B.90 C.12 1.1807 B.91 C.12 1.1808 B.92 C.121.1809 B.93 C.12 1.1810 B.94 C.12 1.1811 B.95 C.12 1.1812 B.96 C.121.1813 B.97 C.12 1.1814 B.98 C.12 1.1815 B.99 C.12 1.1816 B.100 C.121.1817 B.101 C.12 1.1818 B.102 C.12 1.1819 B.103 C.12 1.1820 B.104 C.121.1821 B.105 C.12 1.1822 B.106 C.12 1.1823 B.107 C.12 1.1824 B.108 C.121.1825 B.109 C.12 1.1826 B.110 C.12 1.1827 B.111 C.12 1.1828 B.112 C.121.1829 B.113 C.12 1.1830 B.114 C.12 1.1831 B.115 C.12 1.1832 B.116 C.121.1833 B.117 C.12 1.1834 B.118 C.12 1.1835 B.119 C.12 1.1836 B.120 C.121.1837 B.121 C.12 1.1838 B.122 C.12 1.1839 B.123 C.12 1.1840 B.124 C.121.1841 B.125 C.12 1.1842 B.126 C.12 1.1843 B.127 C.12 1.1844 B.128 C.121.1845 B.129 C.12 1.1846 B.130 C.12 1.1847 B.131 C.12 1.1848 B.132 C.121.1849 B.133 C.12 1.1850 B.134 C.12 1.1851 B.135 C.12 1.1852 B.136 C.121.1853 B.137 C.12 1.1854 B.138 C.12 1.1855 B.139 C.12 1.1856 B.140 C.121.1857 B.141 C.12 1.1858 B.142 C.12 1.1859 B.143 C.12 1.1860 — C.11.1861 — C.2 1.1862 — C.3 1.1863 — C.4 1.1864 — C.5 1.1865 — C.6 1.1866— C.7 1.1867 — C.8 1.1868 — C.9 1.1869 — C.10 1.1870 — C.11 1.1871 —C.12

The specific number for each single composition is deductible asfollows:

Composition 1.777 for example comprises the uracil Ia48, metamitron(B.62) and fenchlorazole (C.5) (see table 1, entry 1.777; as well astable B, entry B.62 and table C, entry C.5).

Composition 2.777 for example comprises the uracil Ib48, metamitron(B.62) and fenchlorazole (C.5) (see the definition for compositions 2.1to 2.1871 below as well as table 1, entry 1.777; table B, entry B.62 andtable C, entry C.5).

Composition 7.777 for example comprises imazapic (B30), and the uracilIa48, metamitron (B.62) and fenchlorazole (C.5) (see the definition forcompositions 7.1 to 7.1871 below as well as table 1, entry 1.777; tableB, entry B.62 and table C, entry C.5).

Also especially preferred are compositions 2.1. to 2.1871 which differfrom the corresponding compositions 1.1 to 1.1871 only in that theycomprise as the active compound A the uracil Ib48.

Also especially preferred are compositions 3.1. to 3.1871 which differfrom the corresponding compositions 1.1 to 1.1871 only in that theycomprise as the active compound A the uracil Ic48.

-   -   Also especially preferred are compositions 4.1. to 4.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.2 as further herbicide B.    -   Also especially preferred are compositions 5.1. to 5.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.7 as further herbicide B.    -   Also especially preferred are compositions 6.1. to 6.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.29 as further herbicide B.    -   Also especially preferred are compositions 7.1. to 7.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.30 as further herbicide B.    -   Also especially preferred are compositions 8.1. to 8.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.31 as further herbicide B.    -   Also especially preferred are compositions 9.1. to 9.1871 which        differ from the corresponding compositions 1.1 to 1.1871 only in        that they additionally comprise B.32 as further herbicide B.    -   Also especially preferred are compositions 10.1. to 10.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.33 as further        herbicide B.    -   Also especially preferred are compositions 11.1. to 11.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.40 as further        herbicide B.    -   Also especially preferred are compositions 12.1. to 12.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.44 as further        herbicide B.    -   Also especially preferred are compositions 13.1. to 13.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.45 as further        herbicide B.    -   Also especially preferred are compositions 14.1. to 14.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.52 as further        herbicide B.    -   Also especially preferred are compositions 15.1. to 15.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.53 as further        herbicide B.    -   Also especially preferred are compositions 16.1. to 16.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.54 as further        herbicide B.    -   Also especially preferred are compositions 17.1. to 17.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.55 as further        herbicide B.    -   Also especially preferred are compositions 18.1. to 18.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.56 as further        herbicide B.    -   Also especially preferred are compositions 19.1. to 19.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.57 as further        herbicide B.    -   Also especially preferred are compositions 20.1. to 20.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.60 as further        herbicide B.    -   Also especially preferred are compositions 21.1. to 21.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.65 as further        herbicide B.    -   Also especially preferred are compositions 22.1. to 22.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.66 as further        herbicide B.    -   Also especially preferred are compositions 23.1. to 23.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.69 as further        herbicide B.    -   Also especially preferred are compositions 24.1. to 24.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.72 as further        herbicide B.    -   Also especially preferred are compositions 25.1. to 25.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.73 as further        herbicide B.    -   Also especially preferred are compositions 26.1. to 26.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.76 as further        herbicide B.    -   Also especially preferred are compositions 27.1. to 27.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.77 as further        herbicide B.    -   Also especially preferred are compositions 28.1. to 28.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.82 as further        herbicide B.    -   Also especially preferred are compositions 29.1. to 29.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.83 as further        herbicide B.    -   Also especially preferred are compositions 30.1. to 30.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.86 as further        herbicide B.    -   Also especially preferred are compositions 31.1. to 31.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.86 and B.54 as further        herbicides B.    -   Also especially preferred are compositions 32.1. to 32.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.86 and B.60 as further        herbicides B.    -   Also especially preferred are compositions 33.1. to 33.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.86 and B.66 as further        herbicides B.    -   Also especially preferred are compositions 34.1. to 34.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 87 as further        herbicide B.    -   Also especially preferred are compositions 35.1. to 35.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 87 and B.54 as        further herbicides B.    -   Also especially preferred are compositions 36.1. to 36.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 87 and B.60 as        further herbicides B.    -   Also especially preferred are compositions 37.1. to 37.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 87 and B.66 as        further herbicides B.    -   Also especially preferred are compositions 38.1. to 38.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.89 as further        herbicide B.    -   Also especially preferred are compositions 39.1. to 39.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 90 as further        herbicide B.    -   Also especially preferred are compositions 40.1. to 40.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 90 and B.54 as        further herbicides B.    -   Also especially preferred are compositions 41.1. to 41.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 90 and B.60 i as        further herbicides B.    -   Also especially preferred are compositions 42.1. to 42.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B. 90 and B.66 as        further herbicides B.    -   Also especially preferred are compositions 43.1. to 43.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.92 as further        herbicide B.    -   Also especially preferred are compositions 44.1. to 44.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.93 as further        herbicide B.    -   Also especially preferred are compositions 45.1. to 45.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.93 and B.54 as further        herbicides B.    -   Also especially preferred are compositions 46.1. to 46.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.93 and B.60 as further        herbicides B.    -   Also especially preferred are compositions 47.1. to 47.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.93 and B.66 as further        herbicides B.    -   Also especially preferred are compositions 48.1. to 48.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 as further        herbicide B.    -   Also especially preferred are compositions 49.1. to 49.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.54 as further        herbicides B.    -   Also especially preferred are compositions 50.1. to 50.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.76 as further        herbicides B.    -   Also especially preferred are compositions 51.1. to 51.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.86 as further        herbicides B.    -   Also especially preferred are compositions 52.1. to 52.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.87 as further        herbicides B.    -   Also especially preferred are compositions 53.1. to 53.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.90 as further        herbicides B.    -   Also especially preferred are compositions 54.1. to 54.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.93 as further        herbicides B.    -   Also especially preferred are compositions 55.1. to 55.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.97 and B.105 as        further herbicides B.    -   Also especially preferred are compositions 56.1. to 56.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.100 as further        herbicide B.    -   Also especially preferred are compositions 57.1. to 57.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.103 as further        herbicide B.    -   Also especially preferred are compositions 58.1. to 58.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.105 as further        herbicide B.    -   Also especially preferred are compositions 59.1. to 59.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.108 as further        herbicide B.    -   Also especially preferred are compositions 60.1. to 60.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.109 as further        herbicide B.    -   Also especially preferred are compositions 61.1. to 61.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.110 as further        herbicide B.    -   Also especially preferred are compositions 62.1. to 62.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.112 as further        herbicide B.    -   Also especially preferred are compositions 63.1. to 63.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.114 as further        herbicide B.    -   Also especially preferred are compositions 64.1. to 64.1871        which differ from the corresponding compositions 11.1 to 1.1871        only in that they additionally comprise B.115 as further        herbicide B.    -   Also especially preferred are compositions 65.1. to 65.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.119 as further        herbicide B.    -   Also especially preferred are compositions 66.1. to 66.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.121 as further        herbicide B.    -   Also especially preferred are compositions 67.1. to 67.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.122 as further        herbicide B.    -   Also especially preferred are compositions 68.1. to 68.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.124 as further        herbicide B.    -   Also especially preferred are compositions 69.1. to 69.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.125 as further        herbicide B.    -   Also especially preferred are compositions 70.1. to 70.1871        which differ from the corresponding compositions 1.1 to 1.1871        only in that they additionally comprise B.132 as further        herbicide B.

EXAMPLES

Hereinbelow, the preparation of the uracils of the formula I isillustrated by examples; however, the subject matter of the presentinvention is not limited to the examples given.

Example 11-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione(compound Ia48)

1.1: 2-amino-5-fluorophenol

To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in ethanol under N₂atmosphere was added palladium on carbon (10 wt %, 250 mg, 0.235 mmol).The mixture was flushed with H₂ and stirred at RT under H₂ (balloon)until complete conversion according to thin layer chromatography (TLC)analysis. Pd/C was removed by filtration and the filtrate wasconcentrated to yield 21.6 g of the title compound.

¹H NMR (DMSO): 4.5 (br, 2H), 6.35 (dd, 1H), 6.45 (dd, 1H), 6.50 (dd,1H), 9.5 (br, 1H).

1.2: 2-bromo-2,2-difluoro-N-(4-fluoro-2-hydroxyphenyl)acetamide

Alternative a)

To 2-amino-5-fluorophenol (14 g, 110 mmol) in dry tetrahydrofuran at 0°C. was added sodium hydride (55 wt % in mineral oil; 4.81 g, 110 mmol).The resulting mixture was stirred for 15 minutes at −15° C. Subsequentlyethyl 2-bromo-2,2-difluoroacetate (24.59 g, 121 mmol) was added dropwiseand the resulting mixture was stirred at 0° C. for two hours. Thereaction mixture was quenched with saturated aqueous NH₄Cl solution andextracted with ethyl acetate. The combined extracts were washed withbrine, dried with Na₂SO₄ and concentrated to yield 33 g of the titlecompound.

¹H NMR (DMSO): 3.3 (br, 1H), 6.8 (m, 2H), 7.25 (dd, 1H), 10.4 (br, 1H).

Alternative b)

To 2-amino-5-fluorophenol (200 mg, 1.573 mmol) in dry tetrahydrofuran at0° C. was added sodium hydride (55 wt % in mineral oil, 68.6 mg, 1.573mmol). The resulting mixture was stirred for 15 minutes at −15° C.Subsequently methyl 2-bromo-2,2-difluoroacetate (327 mg, 1.731 mmol) wasadded dropwise and the resulting mixture was stirred at 0° C. for twohours. The reaction mixture was quenched in saturated aqueous NH₄Clsolution and extracted with ethyl acetate. The combined extracts werewashed with brine, dried with Na₂SO₄ and concentrated to yield 450 mg ofthe title compound

¹H NMR (DMSO): 3.3 (br, 1H), 6.8 (m, 2H), 7.25 (dd, 1H), 10.4 (br, 1H).

1.3: 2,2,7-trifluoro-2H-benzo[b][1,4]oxazin-3(4H)-one

To 2-bromo-2,2-difluoro-N-(4-fluoro-2-hydroxyphenyl)acetamide (33 g, 116mmol) in dry toluene was added 1,8-diazabicyclo[5.4.0]undec-7-en (DBU,17.51 ml, 116 mmol). The resulting mixture was stirred overnight at 80°C. The reaction was quenched in saturated aqueous NH₄Cl solution andextracted with ethyl acetate. The combined extracts were washed withbrine, dried with Na₂SO₄ and concentrated to afford 24.94 g of the titlecompound.

GCMS m/e (M+)=203

1.4: 2,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

2,2,7-trifluoro-2H-benzo[b][1,4]oxazin-3(4H)-one (2.5 g, 12.31 mmol) wasdissolved in sulfuric acid (40 ml, 750 mmol). The reaction mixture wascooled to 0-5° C. Slowly nitric acid (1.761 ml, 39.7 mmol) was addeddropwise and the temperature was maintained between 0-5° C. The reactionmixture was stirred for 30 min at this temperature. Then the reactionmixture was added dropwise to vigorously stirred cold water. A solid wasformed, which was extracted with dichloromethane. The combined extractswere dried over Na₂SO₄, and concentrated to yield 2.56 g of the titlecompound as a brown solid. GC/MS m/e (M+)=248

¹H-NMR (CDCl₃): 2.90 (br, 1H), 7.15 (d, 1H), 7.80 (d, 1H).

1.5:2,2,7-trifluoro-6-nitro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one

To 2,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (6.9 g, 27.8mmol) and potassium carbonate (4.61 g, 33.4 mmol) in dryN,N-dimethylformamide at RT was dropwise added 3-bromoprop-1-yne (80 wt% in toluene; 4.96 g, 33.4 mmol). The resulting mixture was stirred atRT overnight. The reaction mixture was poured in saturated aqueous NH₄Clsolution and extracted with ethyl acetate. The combined extracts werewashed with aqueous NaCl solution, dried with Na₂SO₄, concentrated andchased with toluene to yield 7.06 g of the title compound as dark brownsolid.

GCMS m/e (M+)=286

1.6:6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one

To ammonium chloride (3.96 g, 74.0 mmol) in water was added iron powder(325 mesh; 4.13 g, 74.0 mmol). To the resulting mixture was added2,2,7-trifluoro-6-nitro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one(7.06 g, 24.67 mmol) in methanol/tetrahydrofuran. The resulting mixturewas stirred vigorously at 70° C. for 2 hours. The reaction was quenchedin water/ethyl acetate under stirring. The resulting 2 phase system wasfiltered and the layers were separated. The water layer was subsequentlyextracted with ethyl acetate. The combined organic phases were washedwith brine, dried with Na₂SO₄ and concentrated to yield 5.15 g of thetitle compound. GCMS m/e (M+)=256

1.7:2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one

To6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one(5.1 g, 19.91 mmol) in dry toluene was dropwise added diphosgene (2.64ml, 21.90 mmol) in dry toluene. The resulting mixture was stirredovernight at reflux. The mixture was concentrated and chased withtoluene and used as such in the next step.

1.8:6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione

A solution of (E)-ethyl 3-amino-4,4,4-trifluorobut-2-enoate (4.24 g,23.2 mmol) was added dropwise at 5° C. under N₂ to a stirred solution ofsodium hydride (1.01 g of a 55% suspension in mineral oil, 23.2 mmol) indry DMF. The light yellow suspension was stirred for 1 hour, whileallowing the reaction mixture to warm to room temperature. After thatperiod, a solution of2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one(6.54 g, 23.2 mmol) in toluene was added dropwise, after which themixture was heated at 80° C. overnight under nitrogen. As LC/MSindicated that the reaction was not fully complete, heating wascontinued for a further 3 hours at 100° C., after which the light brownsolution was concentrated in vacuo. The dark residue was partitionedbetween ethyl acetate and aqueous ammonium chloride solution, and theaqueous phase was extracted with additional ethyl acetate. The combinedorganic fractions were washed with brine and dried over Na₂SO₄.Filtration and evaporation of the solvent gave 10.68 g crude brown oil.This was purified by column chromatography (EtOAc:heptane, 20-60%) togive three fractions in which the desired product was the majorcomponent (present as a mixture of keto and enol tautomers). These threefractions were combined and further purified by column chromatography,eluting with di-isopropyl ether, to give the product (3.0 g) as anoff-white fluffy solid (94% purity according to NMR, with ca. 20%existing as the enol tautomer).

¹H-NMR of the major (keto) tautomer (DMSO): 2.50 (s, 1H), 4.78 (s, 2H),6.47 (s, 1H), 7.72 (m, 2H), 12.86 (br, 1H). The broad peak at 12.86 ppmdisappeared upon H/D exchange (with D₂0).

Alternative procedure for the preparation of the final intermediate,6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione,via the carbamate:

1.7a: Ethyl(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamate

A mixture of6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one(2.0 g, 7.8 mmol) and ethyl chloroformate (1.14 g, 10.5 mmol) in drytoluene was heated to reflux for 2 hours. The mixture was evaporated todryness to obtain a brown solid. Column chromatography (silica, EtOAc:heptane, 1:3) gave the product (1.04 g), which was used without furtherpurification in the next step 1.8a.

1.8a:6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione

Sodium hydride (24.4 mg, 0.61 mmol) was added to a stirred solution ofethyl(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamate(100 mg, 0.31 mmol) in DMF. The mixture was heated to 120° C. for 18hours. The formation of the desired product was confirmed by LC/MSanalysis (the retention time of 1.932 minutes and the mass spectrum wereidentical to those of an authentic sample, prepared via the isocyanate.

1.9:1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione

A solution of dimethyl sulfate (0.36 g, 2.86 mmol) in dichloromethanewas added to a stirred solution of6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione(1.0 g, 2.4 mmol) and diisopropylethylamine (0.62 g, 4.8 mmol) indichloromethane at room temperature. The resulting reaction mixture washeated to 50° C. (external temperature). After stirring for 1 hour atthis temperature, thin layer chromatography (tic) analysis indicatedcomplete conversion. The mixture was diluted with dichloromethane andwashed with 1N HCl and saturated bicarbonate solution. The organic phasewas dried (Na₂SO₄) and evaporated to dryness, giving the crude productas a brown oil. Column chromatography (EtOAc: heptane, 10-45%) affordeda white foam. This was further purified by preparative liquidchromatography to give two fractions:

Fraction 1 (229 mg, purity 93%), and Fraction 2 (264 mg, purity 90%).

¹H-NMR of Fraction 1 (DMSO): 2.36 (s, 1H), 3.57 (s, 3H), 4.74 (s, 2H),6.39 (s, 1H), 7.1-7.2 (m, 2H).

Use Examples

The herbicidal activity of the uracils of the formula I was demonstratedby the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this has been impaired bythe active ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. For this purpose, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A goodherbicidal activity is given at values of at least 70 and a very goodherbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments belonged to the followingspecies:

Bayer Code Scientific name Common name ABUTH Abutilon theophrastivelvetleaf AMARE Amaranthus retroflexus common amaranth BRADE Brachiariadeflexa — BRAPL Brachiaria plantaginea alexandergrass CHEAL Chenopodiumalbum lambsquarters COMBE Commenline benghalensis bengal commenlinaDIGSA Digitaria sanguinales large crabcrass ELEIN Eleusine indicawiregrass ERICA Erigeron canadensis Canada horseweed PHBPU Pharbitispurpurea common morning glory SETFA Setaria faberi giant foxtail SETVISetaria viridis green foxtail SOLNI Solanum nigrum black nightshade

At an application rate of 6.25 g/ha, the compound Ia48 applied by thepost-emergence method, showed very good herbicidal activity againstAbutilon theophrasti, Amaranthus retroflexus, Chenopodium album andPharbitis purpurea.

At an application rate of 6.25 g/ha, the compound Ia48 applied by thepre-emergence method, showed very good herbicidal activity againstAmaranthus retroflexus, Erigeron Canadensis and Solanum nigrum.

TABLE 2 Synergistic herbicidal action of the mixture 1.54 applied by thepost- emergence method application rate a.s. herbicidal activity againstin g/ha BRAPL COMBE Ia48 B.54 found calculated found calculated 6.25 —60 — — — 3.12 — — — 60 — — 250 20 — 70 — 6.25 250 85 68 — — 3.12 250 — —95 88

TABLE 3 Synergistic herbicidal action of the mixture 1.93 applied by thepost- emergence method herbicidal activity against application rate a.s.in g/ha BRADE Ia48 B.93 found calculated 6.25 — 85 — — 3.1 65 — 6.25 3.195 95

TABLE 4 Synergistic herbicidal action of the mixture 1.98 applied by thepost- emergence method herbicidal activity against application rate a.s.in g/ha ELEIN Ia48 B.98 found calculated 3.12 — 20 — — 135 60 — 6.25 13575 68

TABLE 5 Synergistic herbicidal action of the mixture 1.118 applied bythe post- emergence method herbicidal activity against application ratea.s. in g/ha DIGSA Ia48 B.118 found calculated 6.25 — 65 — — 12.5 35 —6.25 12.5 85 77

TABLE 6 Synergistic herbicidal action of the mixture 26.98 applied bythe post-emergence method herbicidal activity against application ratea.s. in g/ha SETVI ERICA Ia48 B.76 B.98 found calculated foundcalculated 12.5 — — 95 — 90 — — 1.56 — 0 — 45 — — — 68 90 — 80 — 12.51.56 68 100 100 100 99

TABLE 7 Comparison of the herbicidal activity of example 1 of thepresent invention and example 39 known from WO 90/15057 at anapplication rate of 0.025 kg/ha pre-emergence eight days after treatment(greenhouse) compound example 1 of the present invention  

example 39 known from WO 90/15057  

application rate [kg/ha] 0.025 0.025 unwanted plants damages Pharbitispurpurea 90 80 Setaria faberi 98 90

The test data clearly indicate that the introduction of halogen atoms in2-positions of the benzo[1,4]oxazine ring results in a superiorherbicidal activity as achieved by example 39 known from WO 90/15057,wherein the benzo[1,4]oxazine ring is unsubstituted in the 2-position.

The invention claimed is:
 1. A compound of formula I

wherein R¹ is hydrogen or halogen; R² is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy orC₃-C₆-cycloalkyl-C₁-C₆-alkyl; R³ is hydrogen or halogen; R⁴ is halogen;R⁵ is hydrogen, NH₂, C₁-C₆-alkyl or C₃-C₆-alkynyl; R⁶ is hydrogen,C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁷ is hydrogen or C₁-C₆-alkyl; X is O orS; and Y is O or S; or an agriculturally acceptable salt.
 2. Thecompound of claim 1 wherein R¹ is halogen.
 3. The compound of claim 1wherein R⁴ is F.
 4. The compound of claim 1, wherein R² is C₃-C₆-alkynylor C₃-C₆-haloalkynyl.
 5. A process for preparing the compound of claim1, comprising reacting a compound of formula II

wherein R¹ is hydrogen or halogen; R² is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl,C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy orC₃-C₆-cycloalkyl-C₁-C₆-alkyl; R³ is hydrogen or halogen; R⁴ is halogen;X is O or S; and Y is O or S; with a compound of formula III

wherein R⁵ is hydrogen, NH₂, C₁-C₆-alkyl or C₃-C₆-alkynyl; R⁶ ishydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁷ is hydrogen or C₁-C₆-alkyl;L¹ is C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy,C₁-C₄-alkylthio-C₂C₄alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-haloalkenyloxy,C₃-C₆-alkynyloxy, C₃-C₆-haloalkynyloxy, C₃-C₆-cycloalkyloxy,C₁-C₆-cyanoalkoxy or benzyloxy, which may itself be partly or fullyhalogenated on the phenyl ring and/or may be substituted by from one tothree radicals from the group of cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxyand C₁-C₄-alkylthio to yield the compound of claim
 1. 6. The process ofclaim 5, wherein R¹ is halogen.
 7. The process of claim 5, wherein R⁴ isF.
 8. The process of claim 5, wherein R² is C₃-C₆-alkynyl orC₃-C₆-haloalkynyl.
 9. A herbicidal composition comprising a herbicidalactive amount of a compound of claim 1 and at least one further activecompound selected from the group of the herbicides B and/or safeners C.10. The composition according to claim 9 comprising at least two furtheractive compounds selected from the group of the herbicides B and/orsafeners C.
 11. A herbicidal composition comprising a herbicidal activeamount of a compound of claim 1, and at least one inert liquid and/orsolid carrier and, if appropriate, at least one surface-activesubstance.
 12. The composition of claim 11, wherein R¹ is halogen. 13.The composition of claim 12, wherein R⁴ of the compound of formula I isF and R² is C₃-C₆-alkynyl or C₃-C₆-haloalkynyl.
 14. A method ofcontrolling undesired vegetation, which comprises allowing a herbicidalactive amount of a composition comprising the compound of claim 1 to acton plants, their environment or on seed.
 15. The method of claim 14,wherein the composition further comprises at least one further activecompound selected from the group of the herbicides B and/or safeners C.16. The method of claim 14, wherein the composition further comprises atleast two further active compounds selected from the group of theherbicides B and/or safeners C.
 17. The method of claim 14, wherein thecomposition comprises at least one inert liquid and/or solid carrierand, if appropriate, at least one surface-active substance.
 18. Themethod of claim 17, wherein R¹ of the compound of formula I is halogen.19. The method of claim 18, wherein R⁴ of the compound of formula I isF.
 20. The method of claim 19, wherein R² of the compound of formula Iis C₃-C₆-alkynyl or C₃-C₆-haloalkynyl.